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Sorbic acid

pharmaceutical raw materials
Sorbic acid structure

Sorbic acid 

structure
  • CAS No:

    110-44-1

  • Formula:

    C6H8O2

  • Chemical Name:

    Sorbic acid

  • Synonyms:

    2,4-Hexadienoic acid,(2E,4E)-;Sorbic acid;2,4-Hexadienoic acid,(E,E)-;(2E,4E)-2,4-Hexadienoic acid;(E,E)-1,3-Pentadiene-1-carboxylic acid;Sorbistat;trans,trans-Sorbic acid;α-trans-γ-trans-Sorbic acid;trans,trans-2,4-Hexadienoic acid;(E,E)-2,4-Hexadienoic acid;Panosorb;E 200;2E,4E-Hexadienoic acid;NSC 35405;NSC 49103;NSC 50268;SO 215;2,4-Hexadienoic acid;Sorbinic acid;(2E,4E)-Hexa-2,4-dienoic acid;91751-55-2;1197240-56-4

  • Categories:

    Cosmetic Ingredient  >  Cosmetic Preservative

Description

Sorbic acid, isolated from Sorbus aucuparia, is a naturally occurring, highly efficient, and nonpoisonous food preservative. Sorbic acid generally is an effective inhibitor of most molds and yeasts and some bacteria[1].


Sorbic acid appears as white powder or crystals. Melting point 134.5°C. Slightly acidic and astringent taste with a faint odor.|DryPowder|Colourless needles or white free flowing powder, having a slight characteristic odour and showing no change in colour after heating for 90 minutes at 105 °C|Solid|WHITE CRYSTALLINE POWDER.|White, free-flowing powder


Sorbic acid appears as white powder or crystals. Melting point 134.5°C. Slightly acidic and astringent taste with a faint odor.|Sorbic acid is a hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring. It is a hexadienoic acid, a polyunsaturated fatty acid, a medium-chain fatty acid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a sorbate.|Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.

Sorbic acid Basic Attributes

112.12700

112.13

618-788-5

X045WJ989B

1284

DTXSID3021277

Colorless needles or white powder|Needles from water|Needles form dilute alcohol|White crystalline solid|White crystals or powder

2916190090

Characteristics

37.30000

1.3

Sorbic acid appears as white powder or crystals. Melting point 134.5°C. Slightly acidic and astringent taste with a faint odor.

1.204 g/cm3 @ Temp: 19 °C

134.5 °C

90-92 °C @ Press: 35 Torr

127ºC

1.488

H2O: 1.6 g/L (20 ºC)

2-8ºC

0.01 mm Hg ( 20 °C)

Relative vapour density (air = 1): 3.87

The dry finely powdered acid is a significant dust explosion hazard.

Relatively odorless

Relatively tasteless

Henry's Law constant = 2.9X10-8 atm-cu m/mole at 25 °C (est)

pKa = 4.76 at 25 °C

Sorbic acid begins to sublime above 60 °C.|Sorbic acid is volatile in steam without decomposition.|Hydroxyl radical reaction rate constant = 5.3X10-17 cu cm/molec-sec at 25 °C (est)|Gas-phase ozone reaction rate constant = 5.0X10-11 cu cm/molec-sec at 25 °C (est)

Soluble in hot water [Handbook of Chemistry and Physics]. May be sensitive to exposure to air and heat. The dust may become explosive, particularly when mixed with free-radical initiators or oxidizing agents. (NTP, 1992).

Acids, Carboxylic

SORBIC ACID may discolor on exposure to light. Can react with oxidizing agents. Also incompatible with bases and reducing agents. The dust may become explosive, particularly when mixed with free-radical initiators or oxidizing agents (NTP, 1992).

-3107 kJ/mol

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

NONH for all modes of transport

1

R36/38

S24/25

WG2100000

Xi

Well closed.

Stability Material saturated with this acid may ignite spontaneously. Incompatible with strong oxidizing agents. May be light sensitive.

P261-P305 + P351 + P338

H315-H319-H335

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.

Incompatible materials: Bases, oxidizing agents, reducing agents.|Can react with oxidizing materials.

Sorbic acid used as a chemical preservative in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.|Sorbic acid used as a chemical preservative in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

This chemical is combustible. (NTP, 1992)|Combustible. Finely dispersed particles form explosive mixtures in air.

|Warning|H315 (87.69%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2222 companies from 42 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. Store away from oxidizing materials. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)|Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Combustible when exposed to heat or flame.

The dry finely powdered acid is a significant dust explosion hazard.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|To fight fire, use water.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for SORBIC ACID (6 total), please visit the HSDB record page.

A 4 hour semiocclusive application of sorbic acid to the intact skin of three rabbits did not produce erythema nor edema. The test material was classified as not skin irritating to rabbit skin according to Draize classification scheme.|Sorbic acid was not a primary irritant or sensitizer when applied in 0.1 M concentrations to guinea pig skin. It was characterized as a severe irritant following application of 1 mg to rabbit skin.|Ocular irritation associated with the use of a hydrogel lens care system containing 0.10% sorbic acid was observed in 15% of 135 patients.|Sorbic acid is irritating to the eyes of the rabbits ...

Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. Personal protection: P2 filter respirator for harmful particles.

Well closed.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract.

Repeated or prolonged contact may cause skin sensitization.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles or eye protection in combination with breathing protection.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Sorbic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Sorbic acid has been identified in tobacco smoke(1).

Toxicity

IDENTIFICATION AND USE: Sorbic acid is white crystalline solid or powder. It is used as intermediate for plasticizers and lubricants. In addition, it is used as preservative and antimicrobial agent for foods, cosmetics, and pharmaceuticals. To improve the characteristics of drying oils. In alkyd type coatings to improve gloss. To improve milling characteristics of cold rubber. HUMAN EXPOSURE AND TOXICITY: Application of 150 mg of sorbic acid to human skin for 1 hr produced severe irritation. An allergic response to sorbic acid (2.5% in petrolatum) reportedly occurred in five of 606 eczema patients suspected of having contact sensitivities, who were tested over a 3-year period. Allergic contact dermatitis from sorbic acid has most frequently been reported after the use of topical medicaments such as corticosteroid creams that contain this preservative. Twenty-five cases of contact allergy were reported to Unguentum Merck, most of which were due to sorbic acid. Sorbic acid can also cause stinging and nonimmunologic contact urticarial reactions. Ocular irritation associated with the use of a hydrogel lens care system containing 0.10% sorbic acid was observed in 15% of 135 patients. Genotoxicity studies with HeLa cells and plasmid DNA did not find either mutagenic or genotoxic activities. ANIMAL STUDIES: A 4 hour semiocclusive application of sorbic acid to the intact skin of three rabbits did not produce erythema nor edema. Sorbic acid was not a primary irritant or sensitizer when applied in 0.1 M concentrations to guinea pig skin. It was characterized as a severe irritant following application of 1 mg to rabbit skin. The proliferation and survival of rabbit corneal epithelial cells in tissue culture were reduced in the presence of 0.1% sorbic acid. No adverse effects were noted in rats fed sorbic acid at dietary levels of 1, 2, 4, and 8% for 90 days. Similarly, there were not adverse findings when sorbic acid was fed to puppies at a 4% dietary level for 90 days. Sorbic acid at dietary levels of 1, 5, or 10% for 80 weeks fed to male and female mice and 0, 1.5, or 10% for 2 years fed to male and female rats did not increase the number of deaths or the incidence of spontaneous histological lesions, including tumors. However, mice fed a diet containing 15% sorbic acid for 88 weeks exhibited a high incidence of hepatoma. The hepatomas that developed in mice fed a 15% sorbic acid diet were considered to be induced both by the chronic depletion of the hepatic glutathione and by the gradual production of various promutagens in the intestine which were absorbed and metabolically activated by the liver. There was no adverse effect on the blood or internal organs of rats, guinea pigs, rabbits, and dogs after prolonged feeding at 1 to 500 times the amount used in foods. In developmental studies in rabbits, no treatment-related maternal or developmental effects were observed at 300 mg/kg bw/day. Maternal findings in the mid dose group included increased respiratory rate following administration, decreased body weight gain and rough surface of the spleen. Maternal findings in high dose females included increased respiratory rate following administration, death, abortion, decreased body weight and body weight gain, marked decrease in food consumption and pathological findings upon necropsy (rough surface and reduced size of the spleen). Statistically significant reductions in mean fetal and placental weights and the viability of the fetuses were observed at the mid and high dose levels. Sorbic acid was inactive in vitro in the Syrian hamster embryo (SHE) fibroblast micronucleus test and the SHE cell transformation test. When administered orally at doses up to 5000 mg/kg, sorbic acid increased the frequency of micronuclei in mice. A significant increase in the frequency of sister chromatid exchanges was observed in bone marrow cells of mice following intraperitoneal injection with 75, 100, or 150 mg/kg of sorbic acid, but not with 25 or 50 mg/kg. When mice were fed a diet containing 15% sorbic acid for a period of up to 6 months, ether extracts of the intestinal contents of the mice were not mutagenic to Salmonella typhimurium TA98, but the acidic components obtained by fractionating the either extracts showed slight mutagenic activity after the addition of a metabolic activation system. These results suggested that mutagens were gradually produced in the intestine and moved into the liver where they were metabolically activated. Sorbic acid was negative in the Salmonella reverse mutation assay (Ames test) with and without metabolic activation. Sorbic acid was also negative in the Chinese hamster fibroblast chromosomal aberration test.

The fungicidal activity of sorbic acid against Saccharomyces cerevisiae was enhanced 64-fold in combination with half-minimum fungicidal concentration of polygodial. This synergistic activity of polygodial presumably comes from its ability to inhibit the plasma membrane H+-ATPase.|Sorbic acid has a system of conjugated double bonds which makes it able to undergo nucleophilic addition reactions with certain functions. The interactions between sorbic acid and amine functions present in the endogenous constituents of food were quantified. The formation of new products was demonstrated and the underlying mechanisms studied using ethyl sorbate and various amines. HPLC, GC, GC-SM and NMR analyses of the reaction mixtures enabled the products to be isolated and identified. The addition reactions led, at 20 degrees C, to linear monoadducts and, at 50 degrees C and 80 degrees C, to cyclic derivatives resulting from double addition.|Sorbic acid (E200) and its salts (potassium and calcium sorbate: E202 and E203) are allowed for use as preservatives in numerous processed foods. Sorbic acid had a conjugated system of double bonds which makes it susceptible to nucleophilic attack, sometimes giving mutagenic products. Under conditions typical of food processing (50-80 degrees C), we analyzed the cyclic derivatives resulting from a double addition reaction between sorbic acid and various amines. Mutagenesis studies, involving Ames' test and genotoxicity studies with HeLa cells and plasmid DNA, showed that none of the products studied presented either mutagenic or genotoxic activities.|The objective of this study was to investigate the occurrence of sublethal injury after the pulsed-electric-field (PEF) treatment of two yeasts, Dekkera bruxellensis and Saccharomyces cerevisiae, as well as the relation of sublethal injury to the inactivating effect of the combination of PEF and sorbic acid. PEF caused sublethal injury in both yeasts: more than 90% of surviving D. bruxellensis cells and 99% of surviving S. cerevisiae cells were sublethally injured after 50 pulses at 12 kV/cm in buffer at pHs of both 7.0 and 4.0. The proportion of sublethally injured cells reached a maximum after 50 pulses at 12.0 kV/cm (S. cerevisiae) or 16.5 kV/cm (D. bruxellensis), and it kept constant or progressively decreased at greater electric field strengths and with longer PEF treatments. Sublethally PEF-injured cells showed sensitivity to the presence of sorbic acid at a concentration of 2,000 ppm. A synergistic inactivating effect of the combination of PEF and sorbic acid was observed. Survivors of the PEF treatment were progressively inactivated in the presence of 2,000 ppm of sorbic acid at pH 3.8, with the combined treatments achieving more than log10 5 cycles of dead cells under the conditions investigated. This study has demonstrated the occurrence of sublethal injury after exposure to PEF, so yeast inactivation by PEF is not an all-or-nothing event. The combination of PEF and sorbic acid has proven to be an effective method to achieve a higher level of yeast inactivation. ...|For more Interactions (Complete) data for SORBIC ACID (6 total), please visit the HSDB record page.

LD50 Rat (male) oral >2000 mg/kg bw|LD50 Rat (female) oral >2000 mg/kg bw|LD50 Rat oral 10,500 mg/kg bw|LD50 Rat (male) oral 12,500 mg/kg bw|For more Non-Human Toxicity Values (Complete) data for SORBIC ACID (9 total), please visit the HSDB record page.

Sorbic acid may be obtained from berries of the mountain ash (Sorbus aucuparia L. Rosaceae) where it occurs as the lactone, called parasorbic acid(1). Sorbic acid has been detected in the fruit of Magnolia vine and Rowan berry(2).

Sorbic acid's production and use as a preservative and antimicrobial agent for foods, animal feeds, tobacco, cosmetics, and pharmaceuticals(1,2) may result in its release to the environment through various waste streams(SRC). Sorbic acid has been identified in tobacco smoke(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that sorbic acid is expected to have very high mobility in soil(SRC). The pKa of sorbic acid is 4.76(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Sorbic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 3.08X10-4 mm Hg at 25 °C(5). An 83% of theoretical BOD using activated sludge in a 2-week Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in soil(SRC). Sorbic acid absorbs at wavelengths >290 nm(7) and, therefore, may be susceptible to direct photolysis by sunlight on soil surfaces(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that sorbic acid is not expected to adsorb to suspended solids and sediment(SRC). The pKa of sorbic acid is 4.76(3), indicating that sorbic will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of 1.33(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). An 83% of theoretical BOD using activated sludge in a 2-week Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in water(SRC). Hydrolysis studies found sorbic acid to be hydrolytically stable with the half-lives expected to exceed one year at 25 °C(7). Sorbic acid absorbs at wavelengths >290 nm(8) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Sorbic acid, 0.4 uL/mL, was degraded 23.2% following 5 hours of irradiation by sunlight(9). Sorbic acid is an olefinic compound and olefins in surface waters exposed to sunlight react with photo-oxidants with a half-life on the order of 25 days(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sorbic acid, which has a vapor pressure of 3.08X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase sorbic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.6 hours(SRC), calculated from its rate constant of 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase sorbic acid is also degraded in the atmosphere by reaction with ozone and nitrate radicals. The half-life for the reaction with ozone in air is estimated to be 5.2 hours(SRC), calculated from its rate constant of 5.3X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The half-life for the reaction with nitrate radicals in air is approximated to be 1.4 hours(SRC), calculated from the measured rate constant of 1.34X10-12 cu cm/molecule-sec of an analogous compound (2,4-hexadienal)(4). Sorbic acid absorbs at wavelengths >290 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Sorbic acid, in aqueous solution, was degraded 23.2% following 5 hours of irradiation by sunlight(6).

The rate constant for the vapor-phase reaction of sorbic acid with photochemically-produced hydroxyl radicals has been estimated as 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 7.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of sorbic acid with ozone has been estimated as 5.3X10-17 cu cm/molecule-sec at 25 °C using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.2 hours at an atmospheric ozone concentration of 7X10+11 cu cm/molecule-sec at 25 °C(1). The olefinic structure of sorbic acid suggests that atmospheric night-time reaction with nitrate radicals may have environmental importance(1). By analogy to the structurally similar 2,4-hexadienal, which has a measured nitrate radical rate constant of 1.34X10-12 cu cm/molecule-sec at 25 °C(2), the atmospheric half-life of sorbic acid would be approximately 1.4 hours(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(3). Aqueous hydrolysis studies at 50 °C found sorbic acid to be hydrolytically stable(4); the half-life periods at pH 4, 7 and 9 are expected to exceed one year at 25 °C(4). Sorbic acid absorbs at wavelengths >290 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Sorbic acid, 0.4 uL/mL, was degraded 23.2% following 5 hours of irradiation by sunlight(6). Sorbic acid is an olefinic compound and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(7).

An estimated BCF value of 3 was calculated in fish for sorbic acid(SRC), using a log Kow of 1.33(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of sorbic acid can be estimated to be 9(SRC). According to a classification scheme(2), this estimated Koc value suggests that sorbic acid is expected to have very high mobility in soil. A Koc of less than 1 was estimated for sorbic using an HPLC method(3). The pKa of sorbic acid is 4.76(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

The pKa of sorbic acid is 4.76(3), indicating that sorbic will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). Sorbic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.08X10-4 mm Hg at 25 °C(2).

According to the 2012 TSCA Inventory Update Reporting data, 5 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of sorbic acid (CAS 110-44-1) in the United States may be as low as 10-24 workers and as high as 100-499 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 69,243 workers (21,637 of these are female) are potentially exposed to sorbic acid in the US(1). Occupational exposure may occur through inhalation and dermal contact with sorbic acid at workplaces where sorbic acid is produced or used(SRC). Monitoring and use data indicate that the general population may be exposed to sorbic acid via ingestion of food, inhalation of tobacco smoke and dermal contact with consumer products containing sorbic acid(SRC).

Drug Information

Food Preservatives|The ocular bioavailability of timolol increased in sorbic acid solution due to ion pair formation. Its octanol/water partition coefficient also increased, suggesting the formation of a more lipophilic complex. The concentration of timolol in rabbit aqueous humor was determined after instillation of timolol ophthalmic solution containing sorbic acid. When the molar ratio of sorbic acid to timolol was two or higher, the concentration of timolol in the aqueous humor was higher than with timolol alone. In the presence of sorbic acid the maximal aqueous humor concentration and the area under the curve were more than two-fold higher than those of Timoptol, a timolol maleate ophthalmic solution, and similar in value to TIMOPTIC-XE, a gel-forming ophthalmic solution. To investigate the transcorneal absorption mechanism, in vitro permeation profiles across the intact and de-epithelialyzed cornea were analyzed on the basis of the bilayer diffusion model. The partition coefficient in the epithelium was about twice as high in the presence of sorbic acid than with timolol alone, although the diffusion coefficient in the epithelium did not change. We conclude that the improved ocular bioavailability in the presence of sorbic acid is due to increased partitioning of timolol in the corneal epithelium.

Topical medicaments and cosmetics containing sorbic acid should be avoided. There has been no evidence of flare-ups of eczema from ingestion of foods containing sorbic acid. Therefore, avoiding foods with sorbic acid is unnecessary.

Substances capable of inhibiting, retarding or arresting the process of fermentation, acidification or other deterioration of foods. (See all compounds classified as Food Preservatives.)

Following oral administration of radiolabelled sorbic acid, ... the total recovery of radioactivity was approx. 100% of the low and high doses. The major route of metabolism of sorbic acid was via expired CO2 with approx. 85% of the admininstered radioactivity being recovered as CO2 within 4-10 hours post administration. From the rate and extent of this metabolism, it may be concluded that sorbic acid is rapidly and quantitatively absorbed in the gastrointestinal tract.

Metabolism of sorbic acid in rats is identical to that of normally occurring fatty acids. Under normal conditions of intake, sorbic acid is almost completely oxidized to carbon dioxide and water. Traces (0.1% of dose) may be converted by oxidation to trans,trans-muconic acid.|1,4-Dinitro-2-methylpyrrole, a mutagenic product formed by the interaction of two common food additives, sorbic acid and sodium nitrite, was transformed to 1-nitro-2-methyl-4-aminopyrrole by human fecal mixtures and various intestinal bacterial strains.|Following oral administration of radiolabelled sorbic acid, ... the total recovery of radioactivity was approx. 100% of the low and high doses. The major route of metabolism of sorbic acid was via expired CO2 with approx. 85% of the administered radioactivity being recovered as CO2 within 4-10 hours p.a. From the rate and extent of this metabolism, it may be concluded that sorbic acid is rapidly and quantitatively absorbed in the gastrointestinal tract.

SYMPTOMS: This compound may cause severe irritation. High concentrations are extremely destructive to tissues of the mucous membranes and upper respiratory tract, skin and eyes. The greatest danger from ingestion of large quantities of this compound (2 g/kg) is intestinal obstruction. Aspiration or inhalation could cause chemical pneumonitis. Implantation will cause a foreign body reaction. A case of contact sensitivity has been reported. ACUTE/CHRONIC HAZARDS: This compound is a severe irritant. It is harmful if swallowed or inhaled. High concentrations are extremely destructive to tissues of the mucous membranes and upper respiratory tract, skin and eyes. When heated to decomposition, this compound may emit toxic fumes of carbon monoxide and carbon dioxide. It may produce aldehydes. It may also emit acrid smoke and irritating fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)


Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ Application of 150 mg of sorbic acid to human skin for 1 hr produced severe irritation. ... An allergic response to sorbic acid (2.5% in petrolatum) reportedly occurred in five of 606 eczema patients suspected of having contact sensitivities, who were tested over a 3-year period.|/HUMAN EXPOSURE STUDIES/ Nonimmunologic contact urticaria was studied in 110 patients using the open chamber skin test with sorbic acid (2.5% in petrolatum). Immediate skin reactions were usually seen within 45 min of sorbic acid application; the reaction disappeared within 2 hr following the end of the exposure period.|/HUMAN EXPOSURE STUDIES/ Sorbic aid concentrations (2-isopropanol and water, 1:1) as low as 0.1% produced transient erythema with edema and flare after open or closed application to human skin. Reactions were most intense on the face but also could be produced on the skin of the back, forearm, and deltoid areas. Sorbic acid-induced erythema, edema, and flare were not associated with mast cell degranulation. Aspirin blocked erythematous component, suggesting that prostaglandins are important mediators of this reaction.|/SIGNS AND SYMPTOMS/ Allergic contact dermatitis from sorbic acid has most frequently been reported after the use of topical medicaments such as corticosteroid creams that contain this preservative. Twenty-five cases of contact allergy were reported to Unguentum Merck, most of which were due to sorbic acid. Sorbic acid can also cause stinging and nonimmunologic contact urticarial reactions.|For more Human Toxicity Excerpts (Complete) data for SORBIC ACID (9 total), please visit the HSDB record page.

Acid, Hexadienoic

The substance can be absorbed into the body by inhalation of its aerosol.

Cough. Sore throat.


Redness. Pain.


Redness. Pain. Blurred vision.

Sorbic acid Use and Manufacturing

Methods of Manufacturing

Trimerization of acetaldehyde and catalytic air oxidation of the resulting hexadienal.|In the presence of salts of divalent transition metals as catalysts, ketene and 2-butenal react at 30-80 °C to give a polymeric ester of 3-hydroxy-4-hexenoic acid with a molecular mass greater than or equal to about 2000. This polyester can be cleaved to give sorbic acid in good yield by either bases or acids (e.g., hydrochloric acid); alternatively, cleavage can be effected by metal-complex catalysts.

Uses

Sorbic Acid is an naturally occurring organic compound first isolated from unripe berries. Sorbic acid has been used as a food preservative and as an inhibitor of Clostridium Botulinum bacteria in meat products in order to reduce the amount of nitrites which produce carcinogenic nitroamines.


Processing aids, not otherwise listed


Non-TSCA use

Production

1,000,000 - 10,000,000 lb|(1972) 1.82X10+10 GRAMS (EST)|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2,4-Hexadienoic acid, (2E,4E)-. National Production Volume: 10,000,000 - 50,000,000 lb/yr.

Grades: FCC /Food Chemicals Codex/; technical.

Food, beverage, and tobacco product manufacturing|2,4-Hexadienoic acid, (2E,4E)-: ACTIVE|Only the undissociated form /of sorbic acid/ has antimicrobial activity.|The trans, trans-isomer is usually obtained and is the commercial product.

HPLC determination in cosmetics.|Sorbic acid was one of several organic acids determined by HPLC on bare silica.|AOAC Method 971.15. Sorbic Acid in Cheese. Oxidation Method.|AOAC Method 974.10. Sorbic Acid in Dairy Products. Spectrophotometric Method (Applicable to fresh dairy products - cottage, ricotta, and mozzarella cheese, sour cream, and yogurt).|For more Analytic Laboratory Methods (Complete) data for SORBIC ACID (7 total), please visit the HSDB record page.

An LC-MS method is described for the determination of urinary sorbic acid (SA), a common food additive, which allows to measure down to 4 ug/L of the compound. The method involves an acidic hydrolysis followed by solid-phase extraction. The method was applied to two volunteers who ingested SA and to 36 individuals with no dietary restriction. The results confirm that a little aliquot of ingested SA is found in urine also in humans. The significant correlation found between urinary levels of SA and trans,trans-muconic acid (MA) seems to indicate that the measurement of SA in urine could allow to estimate the amount of MA excreted following a dietary intake of SA and, consequently, to enhance the specificity of MA as a biomarker of benzene exposure. A point of clarification in future studies will be the actual chemical form of SA excreted, since our results clearly demonstrate that without hydrolysis only a very little amount of SA can be found even in subjects heavily exposed to SA.|Sorbic acid (SA: CH(3)-CH=CH-CH=CH-COOH) is one of the widely used food preservatives, although there have been some reports of its toxic activity, for example, on DNA and skin cells. In order to examine the effects of SA on mammalian tissues, we have developed a highly sensitive analytical method using LC/MS/MS with positive and negative ion mode electrospray ionization (ESI). In a previous study, we found that a nonacidic eluent offers better ionization efficiency than acids or their ammoniun salts. However, optimal results could not be obtained because the anion form of SA is poorly retained on a conventional reversed phase column. To resolve this problem, we chose a new type of column and used high-resolution mass spectrometry and positive ion mode analysis. There have only been a few reports using these methods in the positive mode, for example derivatized SA, because acid compounds such as SA are usually used in the negative ion mode. However, a new type of low-carbon-content and polar-endcapped C18 phase column was developed for better separation of SA from the matrix. High-resolution selected reaction monitoring (SRM) gave the best signal to noise ratio in normal-resolution SRM. In the positive ion mode, the CH(3)OH-0.05% HCOOH/0.1% CH(3)COOH eluent system yielded the best ionization efficiency. We propose a highly sensitive and simple analysis using a two-ion-mode ESI SRM method. Such systems should allow quantification of the amount of SA in or around the cells, without the need for pretreatment such as solid phase extraction.|GC-MS determination in urine

EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Food additives|Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Food Additives -> PRESERVATIVE; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]|Cosmetics -> Preservative

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;|Food Additives -> PRESERVATIVE;

Computed Properties

Molecular Weight:112.13
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:112.052429494
Monoisotopic Mass:112.052429494
Topological Polar Surface Area:37.3
Heavy Atom Count:8
Complexity:123
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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