Galactaric acid (HCID 3037582)

Überblick

Galactaric acid is a hexaric acid resulting from formal oxidative ring cleavage of galactose. It has a role as a human metabolite. It is a conjugate acid of a galactarate(1-) and a galactaric acid anion.

Namen und Bezeichner

Bevorzugter Name: Galactaric acid
IUPAC: (2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid
Lokaler Name: Galaktarsure
Englischer Name: Mucic acid
Summenformel: C6H10O8
Molmasse: 210.14

Namen und Synonyme

mucic acidgalactaric acid526-99-8Saccharolactic acidGalactosaccharic acid(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acidSchleimsaureDTXSID7048740MUCILIANCE(2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acidTetrahydroxyadipic acidE149J5OTIF

Weitere Namen anzeigen

meso-galactaric acidD-Mucic acidL-Galactaric acidTETRAHYDROXYHEXANEDIOIC ACIDMucicMucus acid

NSC-81272R,3S,4R,5S-tetrahydroxy-hexanedioic acidDTXCID0028666CHEBI:308522,3,4,5-Tetrahydroxyhexanedioic acidstrontium galactarate mono-hydrateRefChem:633474GlyTouCan:G56286UC

Datenbank-Bezeichner

CAS: 526-99-8
PubChem CID: 3037582
DTXSID: DTXSID7048740
ChEMBL: CHEMBL1232958
ChEBI: CHEBI:30852
UNII: E149J5OTIF
EC Number: 208-404-0
Nikkaji: J6.665F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -2,5
Polarare Oberfläche (TPSA): 156 Å²
H-Brücken-Donoren: 6
H-Brücken-Akzeptoren: 8
Frei drehbare Bindungen: 5
Schwere Atome: 14
Formalladung: 0
Komplexität: 202

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Organic Acids

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]

Color/Form · 2 Einträge

CRYSTALLINE POWDER

PRISMS FROM WATER

Solubility · 4 Einträge

ACICULAR CRYSTALS; SOL IN WATER /AMMONIUM SALT/

SOL IN 300 PARTS COLD WATER, 60 PARTS BOILING WATER; SOL IN ALKALIES; PRACTICALLY INSOL IN ALCOHOL, ETHER

INSOL IN PYRIMIDINE

3.3 mg/mL at 14 °C

Melting Point220 - 225 °C

Physical Description · 2 Einträge

Solid; [Merck Index] Faintly beige powder; [MSDSonline]

Solid

Physikochemische Eigenschaften

Schmelzpunkt: 220 · 220-225 °C (dec.)(lit.)
Siedepunkt: 269.65 °C · 269.65°C (rough estimate)
Dichte: 1.5274 · 1.5274 (rough estimate)
Brechungsindex: 1.58 · 1.5800 (estimate)
storage temp.: Store at RT.
Löslichkeit: 3.3 g/l · 3.3g/l soluble
Aggregatzustand: Solid
pka: 2.99 · 2.99±0.35(Predicted)
Farbe: White to Off-White
Wasserlöslichkeit: Soluble in water.
Merck: 14 · 14,4331
BRN: 1728117 · 1728117
Kosmetik-Inhaltsstoffe Funktionen: CHELATING
InChI: InChI=1/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-
InChIKey: DSLZVSRJTYRBFB-DUHBMQHGNA-N
SMILES: [C@@H](O)([C@@H](O)C(=O)O)[C@@H](O)[C@H](O)C(=O)O |&1:0,2,7,9,r|
CAS Datenbank: 526 · 526-99-8(CAS DataBase Reference)
EPA chemische Informationen: Galactaric acid (526-99-8)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H315 (66.7%): 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 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: Galactaric acid

Galactaric acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

Hazards SummaryOral LD50 (mouse) = 8 gm/kg; [RTECS] May cause irritation; [MSDSonline]

EPA Safer ChemicalChemical: Galactaric acid

Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)

Sicherheitsdaten

wgk: 2
tsca: TSCA listed
hs_code: 29181990
RTECS-Nr.: LW5180000
risk_code: 22-40
hazard_code: Xi,Xn
safety_code: 22-24/25-36/37
Speicherklasse: 11 - Combustible Solids
Giftige Stoffe Daten: 526-99-8(Hazardous Substances Data)

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 5 Einträge

Used as a substitute for tartaric acid, a sequestrant for metal ions (calcium, iron), a retardant of concrete hardening, and a chemical intermediate; Not produced commercially in the US; [HSDB] Proposed as a replacement for potassium bitartrate in baking powder and to make granular effervescing salts; [Merck Index]

Cement Producing [Category: Industry]

SUBSTITUTE FOR TARTARIC ACID; SEQUESTERANT FOR METAL IONS (CALCIUM, IRON)

RETARDS HARDENING OF CONCRETE; INTERMEDIATE FOR SYNTHESIS OF HETEROCYCLIC COMPD (PYRROLES)

RESEARCH CHEMICAL

U.S. Exports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Imports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Production · 2 Einträge

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Methods of Manufacturing · 2 Einträge

PROBABLY BY DEGRADATION OF LACTOSE WITH NITRICACID

PREPD BY OXIDN OF LACTOSE & OF GALACTOSE: KENT, TOLLENS, ANN 227, 221 (1885); MAURER, DREFAHL, BER 75B, 1489 (1942). MFR FROM WOOD SAWDUST: ACREE, BRITISH PATENT 160,777 (1921). REVIEW: BA LEWIS ET AL...IN WHISTLER, WOLFROM, METHODS IN CARBOHYDRATE CHEMISTRY VOL II (ACADEMIC PRESS, NY, 1963) PP 38-46.

Use Classification · 2 Einträge

EPA Safer Chemical Functional Use Classes -> Processing Aids and Additives

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Anwendungen · 3 Einträge

BeschreibungSchleimsäure bildet farblose Kristalle, welche bei 213 ℃ unter Zersetzung schmelzen, und sich nur schlecht in Wasser lösen. Die Verbindung wurde 1780 von Carl Wilhelm Scheele bei der Oxidation von Milchzucker durch Salpetersäure entdeckt und später von Liebig und Pelouze genauer untersucht. Die trockene Destillation von Ammoniummucat liefert Pyrrol.

BeschreibungMucic acid,C6H10O8 or HOOC-(CHOH)4-COOH, (also known as galactaric or meso - galactaric acid) is an aldaric acid obtained by nitric acid oxidation of galactose or galactose - containing compounds like lactose, dulcite, quercite, and most varieties of gum. It forms a crystalline powder, which melts at 230°C. It is insoluble in alcohol, and nearly insoluble in cold water. Due to the symmetry in the molecule, it is optically inactive even though it has chiral carbon atoms (i.e., it is a meso compound). When heated with pyridine to 140°C, it is converted into allommic acid. When digested with fuming hydrochloric acid for some time it is converted into a furfural dicarboxylic acid while on heating with barium sulfide it is transformed into athiophene carboxylic acid. The ammonium salt yields on dry distillation carbon dioxide, ammonia, pyrrol and other substances. The acid when fused with caustic alkalis yields oxalic acid. With potassium bisulfate mucic acid forms 3-hydroxy-2-pyrone by dehydration and decarboxylation.

VerwendenMucic acid can be used to replace tartaric acid in self-rising flour or fizzies.