Bernsteinsure

Succinic Acid

HCID 1110CAS 110-15-6

Grundinformationen

Standard-SMILES
O=C(O)CCC(=O)O
InChIKey
KDYFGRWQOYBRFD-UHFFFAOYSA-N
Summenformel
C4H6O4
Durchschnittliche Molmasse
118,09 g/mol
Monoisotopische Masse
118,02660867

Überblick

Succinic acid appears as white crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Succinic Acid
IUPAC
butanedioic acid
Lokaler Name
Bernsteinsure
Englischer Name
Succinic acid
Summenformel
C4H6O4
Molmasse
118.09

Namen und Synonyme

succinic acidbutanedioic acid110-15-6Amber acidAsuccinWormwood acidDihydrofumaric acidKatasuccinBernsteinsaure1,2-Ethanedicarboxylic acidethylenesuccinic acid1,4-Butanedioic acid
Weitere Namen anzeigen
SAWormwoodSuccnic acidSuccinic acid, 99% 1KG008008-93-3SUCCINIC ACID FCCSiglecSuccinic acid(N)
Succinicum acidumButandisaeureAcidum succinicumButanedionic acidKyselina jantarovaEthylene dicarboxylic acidacide succiniqueBernsteinsaeure

Datenbank-Bezeichner

CAS
110-15-6
PubChem CID
1110
DTXSID
DTXSID6023602
ChEMBL
CHEMBL576
ChEBI
CHEBI:15741
UNII
AB6MNQ6J6L
EC Number
203-740-4
Nikkaji
J2.879G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,6
Polarare Oberfläche (TPSA)
74,6 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
3
Schwere Atome
8

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Organic Acids
Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Sodium oxybate

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
Cosmetics · 2 Einträge

Cosmetic ingredients (Succinic Acid) -> CIR (Cosmetic Ingredient Review)

Buffering

pHpH = 2.7 (0.1 molar aq soln)
FragrancesFragrance Ingredient (Succinic acid) -> IFRA transparency List

Physikochemische Eigenschaften

Schmelzpunkt
185 °C · 185 °C
Siedepunkt
235 °C · 235 °C
Dichte
1.19 g/mL · 1.19 g/mL at 25 °C(lit.)
Dampfdruck
0 · 0-0Pa at 25℃
Brechungsindex
20 · n20/D 1.4002(lit.)
FEMA
4719 · 4719 | SUCCINIC ACID

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 3.4% (78 of 2311) of reports.

Danger

H318 (82.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, P305+P354+P338, P317, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 2311 reports by companies from 28 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Butanedioic acid

Regulation (EC) No 1831/2003 (amended)

Butanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanedioic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15265

Butanedioic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Butanedioic acid: Human health tier I assessment
Fire HazardsFlash point data for this compound are not available. It is probably combustible. (NTP, 1992)
Fire PotentialAs with most organic solids, fire is possible at elevated temperatures or by contact with an ignition source.
Health HazardsSYMPTOMS: Exposure to this compound can cause irritation of the skin, eyes, mucous membranes and upper respiratory tract.
Hazards Summary · 1 Eintrag

Maximum tolerated dose was 2-2.5% when given in drinking water to rats; Caused severe weight loss in the 10% group, and all the rats died within the first 4 weeks; Has anxiolytic activity when given orally to rats at 3-6 mg/kg; [HSDB] Causes somnolence in lethal-dose feeding studies; [RTECS] A skin, eye, mucous membrane, and upper respiratory tract irritant; [CAMEO] An irritant; [MSDSonline]

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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.

Exposure Control and Personal Protection2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Storage ConditionsKeep tightly closed. /Potassium salt trihydrate/
Nonfire Spill Response · 1 Eintrag

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.

Disposal Methods · 3 Einträge

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.

Toxikologische Informationen

Treatment · 1 Eintrag

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 Eintrag

At acute doses or exposures succinic acid is a skin irritant. Chronically high doses of succinate can lead to succinylation or succination of a variety of enzymes. Partial succinate dehydrogenase deficiency (15% to 50% of normal reference enzyme activity) in skeletal muscle leads to elevated succinate levels and causes mitochondrial myopathy with various symptoms, for example, brain involvement, cardiomyopathy, and/or exercise intolerance.

Ecotoxicity Values · 1 Eintrag

EC50 Daphnia magna (first instar; immobilization) 374.2 mg/L/48 hr (95% confidence limits: 350-400 mg/L); static, 22 °C, hardness: 154.5 mg/L as CaCO3, pH of 7.7, alkalinity of 137.7 mg/L as CaCO3, conductivity of 290.4 umohs/cm, Ca of 32.7 mg/L, Mg of 19.7 mg/L, Na of 2.4 mg/L, and K of 1.3 mg/L

Environmental Fate · 3 Einträge

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).

Food Survey Values · 1 Eintrag

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).

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Regulatorische Informationen

FDA Requirements · 3 Einträge

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.

Atmospheric Standards · 1 Eintrag

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.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 3265 8/PG 3
hs_code
29171990
RTECS-Nr.
WM4900000
risk_code
37/38-41-36/37/38

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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.

Metabolism/Metabolites · 2 Einträge

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.

Succinic acid can be converted into fumaric acid by oxidation via succinate dehydrogenase.

Absorption, Distribution and ExcretionSuccinic acid occurs normally in human urine (1.9-8.8 mg/L).
Tissue LocationsAdipose Tissue
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Succinic Acid

Found in fossils, fungi, and lichens; [Merck Index] Present in nearly all plant and animal tissues; Used to make lacquers, dyes, esters for perfumes, alkyd resins, pharmaceuticals, plasticizers, lubricants, and pesticides; Also used in photography, as a sequestrant in foods, a buffering and neutralizing agent, for radiation dosimetry, and to promote plant growth and increased yields in food crops; [HSDB]

Farming (Pesticides) [Category: Industry]

Organic synthesis, manufacture of lacquers, dyes esters for perfumes, photography, in foods as sequestrant, buffer, neutralizing agent

Flavoring agent /Disodium succinate/

Uses of succinic acid range from scientific applications such as radiation dosimetry and standard buffer solutions to applications in agriculture, food, medicine, plastics, cosmetics, textiles, plating, and waste-gas scrubbing

ImpuritiesASH, 0.1% max; IRON, 10 ppm max; LEAD, 5 ppm max; SULFATES, 0.05% max; HEAVY METALS, 10 ppm max
U.S. Imports(1984) 1.82X10+9 g/CARBOXYLIC ACIDS, NSPF/
U.S. Production2023: 10,000,000 - <25,000,000 lb
Industry UsesLubricating agent
Methods of Manufacturing · 4 Einträge

Hydrogenation of maleic acid, maleic anhydride, or fumaric acid produces good yields of succinic acid.

1,4-Butanediol can be oxidized to succinic acid in several ways: (1) with O2 in an aqueous solution of an alkaline-earth hydroxide at 90-110 °C in the presence of Pd-C; (2) by ozonolysis in aqueous acetic acid; or (3) by reaction with N2O4 at low temperature.

Succinic acid can ... be obtained by phase-transfer-catalyzed reaction of 2-haloacetates, electrolytic dimerization of bromoacetic acid or ester, oxidation of 3-cyanopropanal, and fermentation of n-alkanes.

Succinic acid is derived from fermentation of ammonium tartrate.

Anwendungen · 1 Eintrag

Verwendensuccinic acid is widely use as organic intermediates for the pharmaceutical, engineering plastics, resins etc.. For the synthesis of sedatives, contraceptives and cancer drugs in the pharmaceutical industry. In the chemical industry for the production of dyes, alkyd resin, glass fiber reinforced plastics, ion exchange resins and pesticides.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.

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