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Erythorbic Acid

HCID 54675810
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Grundinformationen

CAS
89-65-6
Standard-SMILES
O=C1O[C@H]([C@H](O)CO)C(O)=C1O
InChIKey
CIWBSHSKHKDKBQ-DUZGATOHSA-N
Summenformel
C6H8O6
Durchschnittliche Molmasse
176,12 g/mol
Monoisotopische Masse
176,03208798

Überblick

D-isoascorbic acid is an ascorbic acid.

Namen und Bezeichner

Bevorzugter Name
Erythorbic Acid
IUPAC
(2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one

Namen und Synonyme

Erythorbic acid89-65-6Isoascorbic acidD-Isoascorbic acidD-Araboascorbic acidD-Erythorbic acidAraboascorbic acidIsovitamin CGlucosaccharonic acidErycorbinNeo-cebicureSaccharosonic acid
Weitere Namen anzeigen
Mercate 5FEMA Number: 2410D-erythro-3-Ketohexonic acid lactoneFEMA No. 2410DTXSID6026537D-erythro-3-Oxohexonic acid lactone2,3-Didehydro-D-erythro-hexono-1,4-lactone(2R)-2-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one

Datenbank-Bezeichner

CAS
89-65-6
PubChem CID
54675810
DTXSID
DTXSID6026537
ChEMBL
CHEMBL486293
ChEBI
CHEBI:51438
UNII
311332OII1
EC Number
201-928-0
Nikkaji
J2.837A

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-1,6
Polarare Oberfläche (TPSA)
107 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
2
Schwere Atome
12
Formalladung
0
Komplexität
232

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Organic Acids
Cosmetics · 2 Einträge

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

Antioxidant

SpringerMaterials PropertiesCrystal structure
Food AdditivesANTIMICROBIAL AGENT, ANTIOXIDANT, COLOR OR COLORING ADJUNCT, CURING OR PICKLING AGENT, FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Color/FormShiny granular crystals from water or dioxane
Solubility · 2 Einträge

Soluble in alcohol, pyridine; moderately soluble in acetone; slightly soluble in glycerol

In water, 40 g in 100 mL water at 25 °C

Decomposition · 2 Einträge

When heated to decomposition it emits acrid smoke and irritating fumes.

Decomposition at 184 °C.

Melting Point · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 51.2% (310 of 605) of all reports.

Warning

H315 (46%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 605 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: D-erythro-Hex-2-enonic acid, .gamma.-lactone

Commission Regulation (EC) 1334/2003 (amended)

D-erythro-Hex-2-enonic acid, .gamma.-lactone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of D-erythro-Hex-2-enonic acid, .gamma.-lactone 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: 05-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12801

D-erythro-Hex-2-enonic acid, .gamma.-lactone: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryEmergency treatment: Non-toxic ingestion; Generally recognized as safe (GRAS) in food; [HSDB] May cause irritation; [MSDSonline]
FDA Requirements · 2 Einträge

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.

Chemie und Industrie

Pharmakologische Informationen

Biological Half-LifeIn dogs, this resulted in a half-life of approximately 30 minutes for erythorbic acid in the plasma.
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Absorption, Distribution and Excretion · 5 Einträge

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.

Verwendung und Herstellung

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About 164 °C to 172 °C with decomposition

Decomposes at 174 °C

Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Optical Rotation · 2 Einträge

[α]D/25 10 % (w/v) aqueous solution between – 16,5° to – 18,0°

Specific optical rotation: -17 deg at 16.5 °C/D (c = 1.8 in 0.01 N HCl); -16.6 deg at 20 °C/D (in water)

Physical Description · 3 Einträge

Other Solid; Dry Powder

White to slightly yellow crystalline solid which darkens gradually on exposure to light

Shiny solid; [Merck Index] White odorless powder; [MSDSonline]

Other Experimental PropertiesCrystals; 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/
Special ReportsWHO; 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]
Hazard Classes and CategoriesSkin Irrit. 2 (46%)
Hazardous Reactivities and IncompatibilitiesIncompatible with chemically active metals such as aluminum, copper, magnesium, and zinc. It is also incompatible with strong bases and strong oxidizing agents.

Sicherheit und Schutzausrüstung

Storage ConditionsErythorbic acid should be stored in an airtight container, protected from light, in a cool, dry place.
Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Interactions · 2 Einträge

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.

Environmental Fate · 3 Einträge

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).

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Soil Adsorption/Mobility · 1 Eintrag

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.

Human Toxicity Excerpts · 3 Einträge

/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/

Artificial Pollution SourcesErythorbic 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).
Environmental Biodegradation · 1 Eintrag

AEROBIC: Utilizing the OECD-screening test, 52% of dissolved organic content was eliminated after a 28 day incubation of erythorbic acid; further degradation may be possible, as a plateau was not visible in the degradation curve(1). These data suggest that biodegradation may be an important environmental fate process(SRC).

Environmental Bioconcentration · 1 Eintrag

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).

Volatilization from Water/Soil · 1 Eintrag

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).

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Acute Exposure/ Sodium erythorbate powder was applied to the intact and abraded skin of six rabbits as a single 2 g/kg dose. A substantial amount of residual compound was observed 24 hours after dosing. No erythema, edema, or other signs of dermal irritation were observed at five of six test sites. One rabbit (abraded skin) had slight (1+) erythema at 24 hours that cleared by 48 hours.

/LABORATORY ANIMALS: Acute Exposure/ Sodium erythorbate powder (100 mg) was instilled into the conjunctival sac of albino rabbits (10 male and 2 female). The eyes of half of the treated rabbits were rinsed after 5 seconds. Reactions were comparable in rinsed and unrinsed eyes, and were slight and transient in nature. One hour after dosing, two of six unrinsed eyes had congestion of the iris, but the iris reacted normally to light. Varying degrees of redness were observed in the lids of all unrinsed eyes. Slight redness of the nictitating membrane or palpebral conjunctiva at the medial canthus was observed in two unrinsed eyes. At one hour, 1+ iritis was observed in one rinsed eye. Five of six rinsed eyes had slight redness that was limited to only the nictitating membrane in three cases. At 24 hours, all eyes were normal, with the exception of one that had slight reddening of the conjunctiva at the medial canthus. All eyes, rinsed and unrinsed, were normal at 48 hours. The mean ocular irritation scores were 0.33/110 (unrinsed eyes) and 0.17/110 (rinsed eyes). /Sodium erythorbate/

/LABORATORY ANIMALS: Acute Exposure/ Sodium erythorbate and ascorbic acid at low concentrations caused NADPH oxidase-induced lipid peroxidation and lysosome labilization. Their actions were additive and occurred via a `cofactor" action. At concentrations greater than 1 mM, the acids inhibited lipid peroxidation and lysosome labilization.

/LABORATORY ANIMALS: Acute Exposure/ Erythorbic acid decreased the viscosity of calf thymus DNA solutions when Cu +2 (as CuSO4) was added. Erythorbic acid, with or without the cupric ion, caused single-and double-strand scissions of DNA that were determined by sucrose density gradient centrifugation. The enediol group has an essential role in nucleic acid degradation.

For more Non-Human Toxicity Excerpts (Complete) data for Erythorbic acid (38 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 Eintrag

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).

Probable Routes of Human Exposure · 2 Einträge

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).

Regulatorische Informationen

FDA Requirements · 2 Einträge

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.

Uses · 6 Einträge

CIR ingredient: Erythorbic Acid

Used as an antioxidant (brewing industry), reducing agent (photography), and flavor; [HSDB] Used as antimicrobial agent for food; [Merck Index] An isomer of ascorbic acid used as a food antioxidant; [REPROTOX]

Photographic Processing [Category: Other]

Erythorbic acid is widely used in food applications as an antioxidant. It is also used in oral pharmaceutical applications as an antioxidant.

Reported uses

Antioxidant especially in brewing industry; reducing agent in photography

U.S. Production · 6 Einträge

2023: 400,000 - <550,000 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#1682]

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.

Consumer UsesPreservative
Industry UsesReducing agent
Methods of Manufacturing · 3 Einträge

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.

Formulations/Preparations · 2 Einträge

Mercate "20", Neo-cebitate. /Sodium Erythorbate/

Grade: FCC.

Household ProductsInformation on 206 consumer products that contain Isoascorbic acid in the following categories is provided:
Use Classification · 5 Einträge

Food additives

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Cosmetics -> Antioxidant

General Manufacturing Information · 5 Einträge

Not Known or Reasonably Ascertainable

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.

Anbieter100 Anbieter

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