Succinic acid

118.08804

118.09

1754069

203-740-4

AB6MNQ6J6L

106449|25949

DTXSID6023602

WHITE MINUTE MONOCLINIC PRISMS|Triclinic or monoclinic prisms

2917190090

74.6

-0.6

White to off-white Powder/Solid

1.572 g/cm³ @ Temp: 25 °C

188 °C

235 °C

>230 °F

1.478

H2O: 80 g/L (20 ºC);soluble in ethanol, ethyl ether, acetone and methanol. Insoluble in toluene, benzene, carbon disulfide, carbon tetrachloride and petroleum ether.

Store at RT.

1.91X10-7 mm Hg @ 25 deg C /extrapolated/

Odorless

Very acid taste

pH = 2.7 (0.1 molar aq soln)

4.21(at 25 °C)

Henry's Law constant = 3.6X10-13 atn-cu m/mol @ 25 °C /Estimated/

pK1 = 4.207, pK2 = 5.635 at 25 °C

122.66 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|119.84 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|119.1 Ų [M-H]-

BUFFERING INDEX: 2.90|STD FREE ENERGY OF ANION FORMATION: -164.97 KCAL FOR AQ SOLN @ 25 °C|Hydroxyl radical reaction rate constant = 2.8X10-12 cu cm/molec-sec @ 25 °C /Estimated/

Slightly water soluble.

Acids, Carboxylic

SUCCINIC ACID reacts exothermically to neutralize bases, both organic and inorganic. Can react with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow in the dry, but systems may absorb water from the air to allow corrosion of iron, steel, and aluminum parts and containers. Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. May initiate polymerization reactions.

-356.32 KCAL/MOLE

Ⅲ

UN 3265 8/PG 3

1

37/38-41-36/37/38

26-36/37/39-37/39-39

WM4900000

Xi

Stable. Substances to be avoided include strong bases, strong oxidizing agents. Combustible.

P280-P305 + P351 + P338

H318

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|SRP: At the time of review, 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.|Incineration: Succinic acid should be combined with paper or other flammable material. An alternate procedure is to dissolve it in a flammable solvent and spray the solutions into the fire chamber.

Substance added directly to human food affirmed as generally recognized as safe (GRAS).|Succinic acid used as a general purpose food additive in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.|Succinic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.

UN 3265 8/PG 3

P280; P305 + P351 + P338 + P310

Flash point data for this compound are not available. It is probably combustible. (NTP, 1992)

|Danger|H318 (82.05%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, P310, and P337+P313|Aggregated GHS information provided by 2301 companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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 store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. (NTP, 1992)

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. (NTP, 1992)

As with most organic solids, fire is possible at elevated temperatures or by contact with an ignition source.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Primary irritant effects are present with a number of ... /aliphatic dicarboxylic/ acids, particularly in concentrated solution or as dusts- sensitization is rare. /Aliphatic dicarboxylic acids/

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. Succinic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Succinic acid has been identified as a component of pulp mill effluent(1). Trace amounts, less than 0.5 mg/l, of succinic acid were detected in industrial waste samples from the Hercules, Inc. plant site near Wilmington, NC(2). Succinic acid was identified in the acidic fraction of sewage and sludge from the Iona Island Sewage Treatment Plant, British Columbia(3). Succinic acid was detected in an automobile exhaust sample from a 1982 Toyota Corolla at a concn of 24.3 nmol/cu m and a diesel exhaust sample from a 1971 Mercedes Benz 220D at a concn of 65.7 nmol/cu m(4). Succinic acid emission rates from pine wood, oak wood, and synthetic logs burned were 0.89 mg/kg, 11.68 mg/kg, and not detected, respectively(5).

Succinic acid was detected in soil samples from the UCLA campus at concns ranging from 17.5 to 33.9 nmol/g and bog sediment collected in the foothills of the western Sierra Nevada Mountains at a concn of 341 nmol/g(1). Succinate was detected in sediment samples from Loch Eil, Scotland(2). Succinate was detected in higher amounts, 42.2 ug/g dry weight, at Station E-70 on Loch Eil which receives a higher input of organic matter from a pulp and paper mill than Station E-24, where succinate was identified at a concn of 0.1 ug/g dry weight(2).

URBAN/SUBURBAN: Succinic acid was detected in Los Angeles air samples, collected in June and Oct 1984, at concns ranging from 0.66 to 2.37 nmol/cu m in West Los Angeles and 1.84 to 2.13 nmol/cu m in downtown Los Angeles(1). Dust samples from downtown Los Angeles and a UCLA campus building contained succinic acid at concns of 268 and 406 nmol/cu m, respectively(1). Succinic acid was detected in aerosol samples from urban Tokyo at an average concn of 37 ng/cu m between 1988-89(2). Succinic acid was detected in airborne aerosols from Schenectady, NY collected during Oct 1991 at concns ranging from 55 to 167 ng/cu m(3). Succinic acid was detected in atmospheric aerosols collected from Tsukuba, Japan(4). The average ambient annual concn of succinic acid in fine particles collected from West Los Angeles, downtown Los Angeles, Pasadena, Rubidoux, and San Nicolas Island, CA in 1982 was 55.0, 66.5, 51.2, 84.1, and <0.02 ng/cu m, respectively(5). The average concn of succinic acid in airborne aerosols collected from Takasaki and Karuizawa, Japan in July 1986 was 25.0 and 21.0 ng/cu m, respectively(6). The average daytime concn of succinic acid in air samples collected from Takasaki and Karuizawa, Japan in July 1986 was 47.1 and 36.4 ng/cu m, respectively(7). The ambient concn of succinic acid in West Los Angeles in Oct. 1982 was 14.1 ng/cu m(8). Aerosol samples collected from Tokyo in Feb and July 1992 contained succinic acid at concns ranging from 139 to 279 ng/cu m(9).|RURAL/REMOTE: Arctic aerosol samples collected near Alert, Canada in 1987-1988 were tested for dicarboxylic acids; succinic acid concentrations ranged from 0.15 to 18 ng/cu m, average concentration of 3.5 ng/cu m, with highest concentrations noted from March to April during the "Arctic sunrise"(1).

Oral rat LD50: 2260 mg/kg

LD50 Rat oral 2260 mg/kg

/AQUATIC SPECIES/ ...A series of insulated, round, stainless steel tubs were used for water baths. The water was obtained from Rochat Creek, and a chemical analysis of the water was made during summer when the stream flows were low. The pH of the water was 7.2, alkalinity was 7 ppm, and hardness was 0-17 ppm. The baths were served by a common refrigerated reservoir through which temperature-controlled water was recirculated. Each tub held 9.5 L plastic aquaria, and each aquarium was aerated by a single stone air-breaker and lined with a disposable polyethylene poultry bag. The bag was closed at the top to prevent fish from escaping. Fish were acclimatized at about the temperatures of the assay vessels. The acclimatizing period varied from 3-24 hours, but most fish were conditioned at least overnight. The test fish were starved during acclimatization and transferred to the assay vessel approximately 2 hours prior to addition of 10 ppm of test substance. Usually 1 squawfish and 1 each of 2 species of salmonid were placed together in 1 vessel in 4 L of water, the load being approximately 5 g of fish/L solution. /The fish used measured 5-10 cm./ Water temperature was taken several times during each test, with only the highest temperature recorded in a 24-hr test period reported. The times at which a fish lost its equilibrium and died were recorded. Equilibrium was defined as lost when a fish was no longer able to remain right-side-up, and death was designated when a fish ceased visible movement. ...In Ptychocheilus oregonensis (Northern squawfish), loss of equilibrium occurred in 4-8 hours at 10 ppm, but was regained by 17 hours. No deaths were reported. At 15 ppm neither loss of equilibrium nor death occurred. In Oncorhynchus tshawytscha and kisutch (Chinook salmon and Coho salmon, silver salmon), neither loss of equilibrium nor death occurred at 10 or 15 ppm.

Succinic acid has been observed in distillate from amber and occurs in fossils, fungi, lichens etc(1). It is a constituent of almost all plant and animal tissues and has also been found in meteorites(2).|Succinic acid is a normal intermediary metabolite and a constituent of the citric acid cycle /Kreb's Cycle/.|It is one of the natural acids found in broccoli, rhubarb, beets, asparagus, fresh meat extracts, sauerkraut and cheese.

Succinic acid's production and use in the manufacture of lacquers, dyes, esters for perfumes, in photography(1) and in foods as a sequestrant, buffer and neutralizing agent(2) 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 11(SRC), determined from a log Kow of -0.59(2) and a regression-derived equation(3), indicates that succinic acid is expected to have very high mobility in soil(SRC). Volatilization of succinic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.6X10-13 atm-cu m/mole(SRC), derived from its vapor pressure, 1.91X10-7 mm Hg(4), and water solubility, 8.32X10+4 mg/L(5). Succinic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1.91X10-7 mm Hg at 25 °C(4). The anion form, which is the dominant form in the environment (pKa 4.16 and 5.6), will also not volatilize(SRC). Succinic acid has been observed to biodegrade in soil at rates ranging from 52 to 89% in 7 days to 71 to 95% in 84 days at an initial concn of 1000 ppm(6), suggesting biodegration may be an important environmental fate process in soil.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of -0.59(2) and a regression-derived equation(3), indicates that succinic 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 3.6X10-13 atm-cu m/mole(SRC), derived from its vapor pressure, 1.91X10-7 mm Hg(4), and water solubility, 8.32X1+4 mg/L(5). One of the pKa values of succinic acid is 4.21(6), indicating that this compound will exist in the dissociated form in the environment and anions generally do not adsorb more strongly to suspended solids and sediment than their neutral counterparts(7), and will not volatilize. According to a classification scheme(8), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Succinic acid, present at 100 mg/L, reached 78% of its theoretical BOD in 14 days using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(10), suggesting biodegradation may be an important environmental fate process in water.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), succinic acid, which has a vapor pressure of 1.91X10-7 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase succinic 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 6 days(SRC), calculated from its rate constant of 2.8X10-12 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(3). Particulate-phase succinic acid may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of succinic acid with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Succinic acid is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). The rate constant for the reaction of succinic acid with hydroxyl radicals in aqueous solution has been measured as 3.1X10+8 L/mol sec(3). This corresponds to a half-life of about 7.1 years(SRC) at an average aqueous hydroxyl radical concentration of 1X10-17 mol/L(4). It is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

An estimated BCF of 3 was calculated for succinic acid (SRC), using a log Kow of -0.59(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentraion in aquatic organisms is low(SRC).

The Koc of succinic acid is estimated as 11(SRC), using a log Kow of -0.59(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that succinic acid is expected to have very high mobility in soil. One of the pKa values of succinic acid is 4.21(4), indicating that this compound will exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5).

The Henry's Law constant for succinic acid is estimated as 3.6X10-13 atm-cu m/mole(SRC) derived from its vapor pressure, 1.91X10-7 mm Hg(1), and water solubility, 8.32X10+4 mg/L(2). This Henry's Law constant indicates that succinic acid is expected to be essentially nonvolatile from water surfaces(3). The anion form, which is the dominant form in the environment (pKa 4.16 and 5.6(4)), will also not volatilize(SRC). Succinic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

DRINKING WATER: Succinic acid was qualitatively detected in drinking water from Ottumwa, IA in Sept 1976(6).|RAIN/SNOW: Succinic acid was identified in rainwater from Niwot Ridge, CO at an unspecified concn(1). Succinic acid was detected in rain and snow samples collected from Southern California at concns ranging from 0.034 to 3.8 uM(2). Rain and snow samples collected from Ithaca, NY and Hubbard Brook, NH between June 1976 and May 1977 contained succinic acid at concns ranging from 0.1 umol/94 cm precipitation to 0.1 umol/75 cm precipitation(3). Wet precipitation samples (snow, sleet, rain) collected from Tokyo in 1992 contained succinic acid at concns ranging from 1.28 ug/l to 95.5 ug/l(4). Succinic acid was identified in treated water at an unspecified concn from an unspecified location(5).

Succinic acid was identified as a flavoring constituent of gari, 0.04% and farine, 0.002%(1). Aerosol emission rates of succinic acid from frying hamburger meat was 2.3 mg/kg of meat cooked; emission rates from charbroiling hamburger was 7.6 mg/kg of meat cooked for extra-lean hamburger (approx. 10.0% fat) and 12.0 mg/kg of meat cooked for regular hamburger (approx. 21% fat)(2).

...CONTACT IS USUALLY IN FORM OF DUST OR CRYSTALS.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 31,198 workers (16,182 of these are female) are potentially exposed to succinic acid in the US(1). Occupational exposure to succinic acid may occur through inhalation and dermal contact with this compound at workplaces where succinic acid is produced or used(SRC). Monitoring data indicate that the general population may be exposed to succinic acid via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing succinic acid(SRC).

For nutritional supplementation, also for treating dietary shortage or imbalance

/EXPTL THER/ Succinic acid (100 mM) significantly inhibited systemic anaphylaxis induced by compound 48/80 /a potent mast cell degranulator/ in mice and dose-dependently inhibited local anaphylaxis activated by anti-dinitrophenyl IgE. Further 10 and 100 mM significantly inhibited histamine release from rat peritoneal mast cells activated by compound 48/80 or anti-dinitrophenyl IgE. In addition succinic acid (0.1 and 1 mM) had a significant inhibitory effect on anti-dinitrophenyl IgE-induced tumor necrosis factor-alpha secretion from rat peritoneal mast cells. The level of cyclic AMP in rat peritoneal mast cells, when succinic acid (100 mM) was added, transiently and significantly increased about 4 times compared with that of basal cells. These results suggest a possible use of succinic acid in managing mast cell-dependent anaphylaxis.

Succinic acid occurs normally in human urine (1.9-8.8 mg/L).

Succinic acid is a normal intermediary metabolite and a constituent of the citric acid cycle. It is readily metabolized when administered to animals, but may be partly excreted unchanged in the urine if large doses are fed.

Succinate is an essential component of the Krebs or citric acid cycle and serves an electron donor in the production of fumaric acid and FADH2. It also has been shown to be a good "natural" antibiotic because of its relative acidic or caustic nature (high concentrations can even cause burns). Succinate supplements have been shown to help reduce the effects of hangovers by activating the degradation of acetaldehyde - a toxic byproduct of alcohol metabolism - into CO2 and H2O through aerobic metabolism. Succinic acid has been shown to stimulate neural system recovery and bolster the immune system. Claims have also been made that it boosts awareness, concentration and reflexes.

ASH, 0.1% max; IRON, 10 ppm max; LEAD, 5 ppm max; SULFATES, 0.05% max; HEAVY METALS, 10 ppm max

SYMPTOMS: Exposure to this compound can cause irritation of the skin, eyes, mucous membranes and upper respiratory tract. ACUTE/CHRONIC HAZARDS: This compound causes skin, eye, mucous membrane and respiratory tract irritation. It emits acrid smoke and fumes when heated to decomposition. (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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/OTHER TOXICITY INFORMATION/ Primary irritant effects are present with a number of ... /aliphatic dicarboxylic/ acids, particularly in concentrated solution or as dusts- sensitization is rare. /Aliphatic dicarboxylic acids/

1,2 Ethanedicarboxylic Acid

Grades: Technical, CP, FCC

All other basic organic chemical manufacturing|Butanedioic acid: ACTIVE

Method: AOAC Method 970.31; Procedure: gas chromatographic method; Analyte: succinic acid; Matrix: eggs; Detection Level: not provided.[|Method: AOAC 948.14; Procedure: ether extraction method; Analyte: succinic acid; Matrix: eggs; Detection Level: not provided.[

Food additives|Food additives -> Flavoring Agents|Food Additives -> FOOD_ADDITIVE; -> JECFA Functional Classes|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]|Cosmetics -> Buffering|Environmental transformation -> Pesticide transformation products (metabolite, successor)

Butanedioic acid is a known environmental transformation product of Sulcotrione.

Flavoring Agents|Food Additives -> FOOD_ADDITIVE;