Galactaric acid (HCID 3037582)

概要

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.

名称と識別子

優先名称: Galactaric acid
IUPAC: (2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid
現地名: 粘液酸
英語名: Mucic acid
分子式: C6H10O8
分子量: 210.14

名称と別名

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

名称をさらに表示

粘液酸2,3,4,5-テトラヒドロキシアジピン酸D-ガラクタル酸L-粘液酸D-粘液酸D-ムチン酸ガラクト糖酸サッカロ乳酸L-ムチン酸L-ガラクタル酸ガラクタル酸ムチン酸D-galacto-ヘキサル酸L-galacto-ヘキサル酸2,3,4,5-テトラヒドロキシヘキサン二酸テトラヒドロキシアジピン酸ムチン酸(粘液酸)(2R,3S,4R,5S)-2,3,4,5-テトラヒドロキシヘキサン二酸(2S,3R,4S,5R)-2,3,4,5-テトラヒドロキシアジピン酸(2S,3R,4S,5R)-2,3,4,5-テトラヒドロキシヘキサン二酸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

データベース識別子

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

物性

構造計算による物性

XLogP: -2.5
極性表面積: 156 Å²
水素結合供与体数: 6
水素結合受容体数: 8
回転可能結合数: 5
重原子数: 14
形式電荷: 0
複雑度: 202

実験および物理化学的性質

Chemical ClassesOther Classes -> Organic Acids

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

Color/Form · 2 件

CRYSTALLINE POWDER

PRISMS FROM WATER

Solubility · 4 件

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 件

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

Solid

物理化学的性質

融点: 220 · 220-225 °C (dec.)(lit.)
沸点: 269.65 °C · 269.65°C (rough estimate)
比重(密度): 1.5274 · 1.5274 (rough estimate)
屈折率: 1.58 · 1.5800 (estimate)
貯蔵温度: Store at RT.
溶解性: 3.3 g/l · 3.3g/l 可溶
外見: 個体
酸解離定数(Pka): 2.99 · 2.99±0.35(Predicted)
色: ホワイトからオフホワイト
水溶解度: 水に溶ける。
Merck: 14 · 14,4331
BRN: 1728117 · 1728117
化粧品成分の機能: キレート化
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 データベース: 526 · 526-99-8(CAS DataBase Reference)
EPAの化学物質情報: Galactaric acid (526-99-8)

化学的性質

化学的特性white to light beige fine crystalline powder

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 2 件

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%)

安全データ

wgk: 2
tsca: TSCA listed
rtecs: LW5180000
hs_code: 29181990
risk_code: 22-40
化審法: (2)-3410
hazard_code: Xi,Xn
safety_code: 22-24/25-36/37
ストレージクラス: 11 - Combustible Solids
有毒物質データの: 526-99-8(Hazardous Substances Data)

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

Uses · 5 件

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 件

(1977) No Data

(1979) No Data

U.S. Imports · 2 件

(1977) No Data

(1979) No Data

U.S. Production · 2 件

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Methods of Manufacturing · 2 件

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 件

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

応用分野 · 3 件

解説粘液酸，無色のプリズム状結晶．融点213～214 ℃，分解点225 ℃．光学不活性．冷水に難溶なのでガラクトースの定性，定量に利用される．エタノールに不溶．水とともに煮沸すると可溶性のDL-γ-ラクトンC6H8O7となり，それを還元するとDL-ガラクトン酸を与える．フェーリング液を還元しないが，銀鏡反応を示す．LD50 8000 mg/kg(マウス，経口)．森北出版「化学辞典（第2版）

説明Mucic 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.

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