Erythorbic acid
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Erythorbic acid
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CAS No:
89-65-6
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Formula:
C6H8O6
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Chemical Name:
Erythorbic acid
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Synonyms:
D-erythro-Hex-2-enonic acid,γ-lactone;Erythorbic acid;D-erythro-Hexonic acid,3-keto-,γ-lactone;Erycorbin;Glucosaccharonic acid;Isoascorbic acid;Isovitamin C;Mercate 5;Saccharosonic acid;D-Araboascorbic acid;Araboascorbic acid,D-;D-(-)-Isoascorbic acid;Araboascorbic acid;D-Isoascorbic acid;Neo-Cebicure;D-Erythorbic acid;D-arabino-Ascorbic acid;NSC 8117;E 315;98966-42-8;74242-57-2
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CAS No:
Description
Erythorbic acid (D-Isoascorbic acid), produced from sugars derived from different sources, such as beets, sugar cane, and corn, is a food additive used predominantly in meats, poultry, and soft drinks.
DryPowder; OtherSolid; PelletsLargeCrystals|White to slightly yellow crystalline solid which darkens gradually on exposure to light
D-isoascorbic acid is an ascorbic acid.
Erythorbic acid Basic Attributes
176.12400
176.12
201-928-0
311332OII1
DTXSID6026537
Shiny granular crystals from water or dioxane
2932209090
Characteristics
107.22000
-1.6
DryPowder; OtherSolid; PelletsLargeCrystals
1.654 g/cm3
174 °C (decomp)
552.7ºC at 760 mmHg
238.2ºC
1.711
In water, 40 g in 100 mL water at 25 deg C
Store at 0-5ºC
1.54X10-10 mm Hg at 25 deg C (est)
[α]D/25 10 % (w/v) aqueous solution between – 16,5° to – 18,0°
Henry's Law constant = 4.07X10-8 atm-cu m/mol at 25 °C (est)
Crystals; soluble in water; pH of aqueous solution between 5-6; 10% solution made from commercial grade may have pH of 7.2-7.9. The free acids is more soluble in water ... than the sodium salt (16 g/100 mL water) /Sodium erythorbate/
Safety Information
NONH for all modes of transport
2
R36/37/38
S24/25
KF3015000
Xi
Stable. Combustible. Incompatible with chemically active metals, aluminium, zinc, copper, magnesium, strong bases, strong oxidizing agents.
P261-P305 + P351 + P338
H315-H319-H335
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Incompatible with chemically active metals such as aluminum, copper, magnesium, and zinc. It is also incompatible with strong bases and strong oxidizing agents.
Erythorbic acid used as a chemical preservative in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.|Erythorbic 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.
WHO; Food Additives Series 28 - Erythorbic acid and its sodium salt (1991).[Available from, as of August 6, 2010: http://www.inchem.org/documents/jecfa/jecmono/v28je03.htm]
|Warning|H315 (94.22%): 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 498 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
The modifying effects of 3 antioxidants, sodium L-ascorbate (SA), ascorbic acid (AA) and sodium erythorbate (SE) on two-stage gastric carcinogenesis in F344 rats initiated with N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) were investigated. Administration of 5% SE in the diet significantly decreased the incidence of dysplasia of the pylorus and, more marginally the incidence of papilloma of the forestomach, whereas administration of 5% and 1% SA and 5% AA in the diet was not associated with effect. These results suggest that SE exerts a weak inhibitory effect on gastric carcinogenesis. /Sodium erythorbate/|The marked azotemia & other evidence of renal damage induced in rats & dogs by rapid iv admin of tetracycline-HCl (50 mg/kg) was prevented by concomitant admin of ascorbic acid (125 mg/kg or more). D-isoascorbic acid had a similar effect when tested in rats.
LD50 Mouse oral 8.3 g/kg|LD50 Rat oral 18.0 g/kg
Erythorbic acid's production and use as an antioxidant, especially in the brewing industry(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that erythorbic acid is expected to have very high mobility in soil(SRC). Volatilization of erythorbic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.07X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Erythorbic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.54X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Utilizing the OECD-screening test, 52% of dissolved organic content was eliminated after a 28 day incubation of erythorbic acid(5), suggesting that biodegradation may be an important fate process in soils(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that erythorbic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.07X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of -1.88(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). This compound contains a cyclic ester functional group which is likely to hydrolyze under alkaline conditions(7). Utilizing the OECD-screening test, 52% of dissolved organic content was eliminated after a 28 day incubation of erythorbic acid(8), suggesting that biodegradation may be an important fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), erythorbic acid, which has an estimated vapor pressure of 1.54X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase erythorbic acid may be removed from the air by wet or dry deposition(SRC). Erythorbic acid does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Erythorbic acid contains a cyclic ester functional group which is likely to hydrolyze under alkaline conditions(1). Erythorbic acid does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3.2 was calculated in fish for erythorbic acid(SRC), using an estimated log Kow of -1.88(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of erythorbic acid can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that erythorbic acid is expected to have very high mobility in soil.
The Henry's Law constant for erythorbic acid is estimated as 4.07X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that erythorbic acid is expected to be essentially nonvolatile from water surfaces(2). Erythorbic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a an estimated vapor pressure of 1.5X10-10 mm Hg(SRC), determined from a fragment constant method(3).
According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in industrial manufacturing, processing, and use of erythorbic acid is 1 to 99; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 10,270 workers (2,087 of these were female) were potentially exposed to erythorbic acid in the US(1). Occupational exposure to erythorbic acid may occur through inhalation and dermal contact with this compound at workplaces where erythorbic acid is produced or used. The general population may be exposed to erythorbic acid primarily via ingestion of food and beverages containing erythorbic acid, and dermal contact with this compound(SRC).
Drug Information
Erythorbic acid is a stereoisomer of l-ascorbic acid, and is used as an antioxidant in foods and oral pharmaceutical formulations. It has approximately 5% of the vitamin C activity of l-ascorbic acid.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)
Erythorbic acid is readily absorbed and metabolized. Following an oral dose of 500 mg of erythorbic acid to human subjects the blood level curves for ascorbic acid and erythorbic acid showed a similar rise. In five human subjects, an oral dose of 300 mg was shown to have no effect on urinary excretion of ascorbic acid.|In hamster, rat and rabbit, for which ascorbate is not an essential vitamin, intestinal absorption of L-ascorbic acid is low and takes place by passive diffusion; conversely, in guinea pig and human, ascorbate absorption is mediated by a saturable, sodium- dependent, active transport mechanism. It follows that the former species are not suitable models for human absorption. Since the active transport system is saturable but since passive diffusion might also be significant at high dose levels, the absorption of ascorbic acid is dose dependent. Erythorbic acid appears to be another but much poorer substrate for the same transport system and may thus act as a weak competitive inhibitor of L-ascorbate uptake. In studies using isolated brush border vesicles from guinea pig ileum, the K1 has variously been estimated at about 11 mM and around 20 mM; this compares with an apparent Km for ascorbate uptake of about 0.3 mM in the same system.|The reason for lack of a stronger antiscorbutic action of erythorbic acid is probably the incapacity of the tissues to retain it in the quantities that ascorbic acid is stored.|The absorption of erythorbic acid through the human buccal mucosa was studied in healthy adult subjects. Absorption of a solution of 10 mM erythorbic acid, buffered to pH 6, was 13.0 +/- 0.74 umol/5 minutes. No statistical difference was found between the absorptions of Erythorbic Acid and L-ascorbic acid.|For more Absorption, Distribution and Excretion (Complete) data for Erythorbic acid (13 total), please visit the HSDB record page.
In dogs, this resulted in a half-life of approximately 30 minutes for erythorbic acid in the plasma.
/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 the 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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 or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/HUMAN EXPOSURE STUDIES/ The influence of erythorbic acid on ascorbic acid metabolism and status was investigated in 11 healthy, non-pregnant women volunteers. The volunteers were maintained in a metabolic unit and fed a formula diet devoid of vitamin C for 54 days. After depletion of 24 days, the subjects received increasing supplements of ascorbic acid (30 mg/d, 60 mg/d and 90 mg/d for successive periods of 10 days) in the presence or absence of 600 mg/d of erythorbic acid. The depletion resulted in a marked decrease in ascorbic acid in all blood indices and during the study some subjects developed signs of scurvy. Ascorbic acid supplements of 30 mg/d for 10 days failed to increase plasma ascorbate concentrations; 60 mg for 10 days caused a small increase and 90 mg/d resulted in a mean ascorbic acid concentration of 29 mmol/L. Erythorbic acid did not cause any adverse effects but rather had a small ascorbic acid-sparing effect.|/HUMAN EXPOSURE STUDIES/ Adult male volunteers received a constant mixed diet which contained 200 g processed meat for 51 days. The processed meats used were uncured sausage, sausage cured with nitrite (156 mg/kg meat) and sausage cured with a mixture of nitrite (156 mg/kg meat) and erythorbic acid (550 mg/kg meat). The dietary treatments had no significant effects on apparent absorption of iron, zinc or copper, nor on serum zinc or copper levels, plasma ferritin, transferrin or ceruloplasmin levels. The authors concluded that commercial curing processes do not adversely affect the bioavailability of zinc or copper in meat.|/GENOTOXICITY/ Sodium erythorbate did not cause chromosomal aberrations or sister chromatid exchanges in cultured human embryo fibroblasts. /Sodium erythorbate/
D-araboascorbic acid
Erythorbic acid Use and Manufacturing
Erythorbic acid is synthesized by the reaction between methyl 2-keto-D-gluconate and sodium methoxide. It can also be synthesized from sucrose and produced from Penicillium spp.|Erythorbic acid can also be prepared by reacting 2-keto-D-gluconate with sodium methoxide, synthesized from sucrose, or naturally produced by Penicililum species. Sodium erythorbate is prepared from D-glucose by a combination of biosynthesis and chemical synthesis via the intermediate 2-keto-D-gluconic acid.|Erythorbic acid is produced by the fermentation of D-glucose to 2-keto-D-gluconic acid by Pseudomonas fluorescens bacteria. The fermentation product is esterified and heated in basic solution to yield sodium erythorbate. Upon acidification of the salt in a water-methanol solution, erythorbic acid is formed.
Antioxidant especially in brewing industry, reducing agent in photography. Used as food antioxidant, has the function of keeping fresh and quality Antioxidants; preservatives; color additives.
Adhesives and sealant chemicals
Adhesives and sealants
1,000,000 - 10,000,000 lb|(1972) Probably > 4.54 x 10+5 g|(1975) Probably > 9.1 x 10+5 g|D-erythro-Hex-2-enonic acid, .gamma.-lactone is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1684]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: D-erythro-Hex-2-enonic acid, .gamma.-lactone. Aggregated National Production Volume: 500,000 to < 1 million lbs.
Mercate "20", Neo-cebitate. /Sodium Erythorbate/|Grade: FCC.
Adhesive manufacturing|D-erythro-Hex-2-enonic acid, .gamma.-lactone: ACTIVE|Has one-twentieth of the vitamin C activity of L-ascorbic acid|...Used to prevent nitrosoamine formation from nitrites in cured meats such as bacon.|Mid regulation, limitations: to accelerate color fixing in cured pork and beef cuts and cured comminuted meat food products; 3/4 ounce to 100 lb meat or meat by-product.
Food additives|Food Additives -> ANTIOXIDANT; -> JECFA Functional Classes|Cosmetics -> Antioxidant
Food Additives -> ANTIOXIDANT;
Computed Properties
Molecular Weight:176.12
XLogP3:-1.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:176.03208797
Monoisotopic Mass:176.03208797
Topological Polar Surface Area:107
Heavy Atom Count:12
Complexity:232
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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