CAS 79-33-4 L-Lactic Acid (HCID 107689)

概要

(S)-lactic acid is an optically active form of lactic acid having (S)-configuration. It has a role as an Escherichia coli metabolite and a human metabolite. It is a (2S)-2-hydroxy monocarboxylic acid and a 2-hydroxypropanoic acid. It is a conjugate acid of a (S)-lactate. It is an enantiomer of a (R)-lactic acid.

名称と識別子

優先名称: L-Lactic Acid
IUPAC: (2S)-2-hydroxypropanoic acid
現地名: L-乳酸
英語名: L(+)-Lactic acid
分子式: C3H6O3
分子量: 90.08

名称と別名

L-Lactic acid79-33-4L-(+)-Lactic acid(S)-Lactic acid(S)-2-Hydroxypropanoic acid(2S)-2-hydroxypropanoic acidSarcolactic acid(S)-2-Hydroxypropionic acid(+)-Lactic acidParalactic acid(S)-(+)-Lactic acidLactic acid, L-

名称をさらに表示

L-乳酸(S)-(+)-乳酸(高純度)(S)-(+)-2-ヒドロキシプロパン酸L-(+)-乳酸(S)-(+)-乳酸(S)-2-ヒドロキシプロピオン酸（S）-2-ヒドロキシプロパン酸(S)‐(+)‐乳酸(高純度)L(+)‐乳酸(2S)-2-ヒドロキシプロパン酸乳酸, L-(+)-L-(+)-乳酸溶液L-乳酸, 90%Ｌ(+)-乳酸2-HYDROXYPROPIONIC ACIDLACTIC ACIph90EspiritinHiPure 90PURAC(R) 50

TisulacPropanoic acid, 2-hydroxy-, (2S)-Sarcolacticum acidumL-(+)-alpha-Hydroxypropionic acidF9S9FFU82NCHEBI:422DTXSID6034689Lactisan Winter

データベース識別子

CAS: 79-33-4
PubChem CID: 107689
DTXSID: DTXSID6034689
ChEMBL: CHEMBL330546
ChEBI: CHEBI:422
UNII: F9S9FFU82N
EC Number: 201-196-2
Nikkaji: J9.134K

物性

構造計算による物性

XLogP: -0.7
極性表面積: 57.5 Å²
水素結合供与体数: 2
水素結合受容体数: 3
回転可能結合数: 1
重原子数: 6
形式電荷: 0
複雑度: 59.1

実験および物理化学的性質

Chemical ClassesOther Classes -> Organic Acids

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesCorrosion

FragrancesFragrance Ingredient (L-Lactic acid (2-hydroxy propionic acid)) -> IFRA transparency List

Melting Point16.8 °C

Physical Description · 3 件

Liquid

Solid; [Merck Index] Hygroscopic solid; [Sigma-Aldrich MSDS]

Liquid

物理化学的性質

融点: 52 · 52-54°C
比旋光度: -13.5 · -13.5 º (c=2.5, 1.5N NaOH)
沸点: 125 °C · 125 °C
比重(密度): 1.206 g/mL · 1.206 g/mL at 25 °C
蒸気圧: 0.038 Pa · 0.038Pa at 25℃
FEMA: 2611 · 2611 | LACTIC ACID
屈折率: 20 · n20/D 1.427
闪点: 230 °F · >230 °F
貯蔵温度: 2 · 2-8°C
溶解性: 2 O: · H2O: 10 mg/mL 無色透明
外見: 粉体・固形
酸解離定数(Pka): 25 °, · pK at 25°, 3.79
色: 白い
臭い (Odor): 無臭の酸性
PH: 2.8 · 2.8 (20°C, 10g/L in H2O)
においのタイプ: 無臭
水溶解度: 溶ける
Merck: 14 · 14,5337
JECFA Number: 930 · 930
BRN: 1720251 · 1720251
InChI: 1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1
InChIKey: JVTAAEKCZFNVCJ-REOHCLBHSA-N
SMILES: C[C@H](O)C(O)=O
LogP: -0.54 at · -0.54 at 20℃
CAS データベース: 79 · 79-33-4(CAS DataBase Reference)
NISTの化学物質情報: -2 · (s)-2-Hydroxypropanoic acid(79-33-4)
EPAの化学物質情報: L-Lactic acid (79-33-4)

化学的性質

化学的特性Crystalline Solid

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1219) of reports.

Danger

H314 (36.1%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

危険有害性情報

Regulatory Information · 4 件

Chemical: Propanoic acid, 2-hydroxy-, (S)-

Propanoic acid, 2-hydroxy-, (2S)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanoic acid, 2-hydroxy-, (2S)- 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: 03-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14252

(S)-2-Hydroxypropanoic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Lactic acid isomers

Hazards Summary · 1 件

Corrosive to rabbit skin, mildly irritating to guinea pig skin, and not irritating to pig skin; Not sensitizing in a study of guinea pigs; A 13-week oral study of rats produced a NOAEL of 500 mg/kg/day (highest tested dose); Studies on reproductive and developmental toxicity not considered necessary because lactic acid is a product of human intermediary metabolism; [EPA ChAMP: Interim Hazard Characterization] An irritant that may cause serious eye injury; [Sigma-Aldrich MSDS]

EPA Safer ChemicalChemical: L-Lactic acid

Hazard Classes and Categories · 5 件

Skin Corr. 1C (36.1%)

Skin irritation - category 2

Skin corrosion/irritation - Category 1

Skin Corr. 1C

毒性情報

Health Effects · 1 件

Chronically high levels of Lactic acid are associated with at least a dozen inborn errors of metabolism including: 2-Methyl-3-hydroxybutyryl CoA dehydrogenase deficiency, Biotinidase deficiency, Fructose-1,6-diphosphatase deficiency, Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease, Glycogenosis, Type IB, Glycogenosis, Type IC, Glycogenosis, Type VI. Hers disease, Lactic Acidemia, Leigh Syndrome, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Pyruvate Decarboxylase E1 Component Deficiency, Pyruvate dehydrogenase complex deficiency, Pyruvate dehydrogenase deficiency, Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency).

Adverse EffectsDermatotoxin - Skin burns.

Toxicity Summary · 1 件

Accumulation of L-lactic acid in the body has been shown to be toxic. At times of lactic acidosis, when excess intracellular lactate is released into the blood, maintenance of electroneutrality of the blood requires that a cation be released into the blood, as well. This can reduce blood pH. Lactate may exert a strong action over GABAergic networks in the developing brain, making them more inhibitory than it was previously assumed, acting either through better support of metabolites, or alterations in base intracellular pH levels, or both. (Wikipedia)

Carcinogen Classification · 2 件

Not listed by IARC.

No indication of carcinogenicity to humans (not listed by IARC).

Toxicity DataLC50 (rat) > 7,940 mg/m3/4hr

安全データ

F: 3-10
wgk: 1
tsca: TSCA listed
rtecs: OD2800000
ridadr: 3261
毒性: LD50 intraperitoneal in mouse: 3194mg/kg
hs_code: 29181100
risk_code: 38-41-34-36/37/38-36-35
化審法: (2)-1369 届出不要化学物質
消防法: 危険物第4類第三石油類(水溶性)
hazard_code: Xi,C
safety_code: 26-39-45-36/37/39-36
hazard_class: 8
packing_group: III
Hazard Classifications: Eye Dam. 1Skin Corr. 1C
ストレージクラス: 8A - Combustible corrosive hazardous materials

化学と産業

薬理情報

Tissue LocationsAll Tissues

Cellular LocationsCytoplasm

Metabolite PathwaysFructose-1,6-diphosphatase deficiency

用途と製造

Uses · 3 件

Occurs naturally in mammals--concentration increases in serum and muscle following exercise; [Merck Index] Used in the agricultural, chemical, leather processing, pharmaceuticals, and cosmetics industries; Used as an electroplating agent, food/feed additive, pH regulator, cleaning/washing agent, disinfectant, and tanning agent; [IUCLID] Used to flavor animal feeds; [ExPub: EFSA - FEEDAP] Used as a solvent and intermediate in chemical production, as a pH regulator in fabric finishing, and in paints, coatings, soaps, and cleaning products; [EPA ChAMP: Hazard Characterization] Used to make large scale and fine chemicals, pulp-paper-paper products, food products, and plastic products, in mining, health services, agriculture-forestry-fishing, and building and construction work; [ExPub: ECHA REACH Registrations] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]

Electroplating [Category: Plate]

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

U.S. Production2023: 1,000,000 - <2,500,000 lb

Consumer UsesProcessing aids not otherwise specified

Industry UsesCleaning agent

Household ProductsInformation on 84 consumer products that contain Propanoic acid, 2-hydroxy-, (2S)- in the following categories is provided:

Use Classification · 3 件

EPA Safer Chemical Functional Use Classes -> Antimicrobial Actives;Chelating Agents;Preservatives and Antioxidants;Processing Aids and Additives

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

Fragrance Ingredients

応用分野 · 5 件

解説L-乳酸は解糖の最終産物としてピルビン酸の還元によって生ずるが、乳酸デヒドロゲナーゼがこの反応を触媒する。柱状晶。融点53℃。比旋光度（＋）2.6度で、吸湿性。休息時にも血液中に正常成分として少量存在するが、運動時には筋肉中のグリコーゲンから大量に生じ、血液中の濃度が増加する。

用途有機合成原料。医薬原料。

用途醸造工業?有機合成原料,食品添加物(飲料用他),乳酸塩?医薬原料 (NITE CHRIP)

使用Occurs in small quantities in the blood and muscle fluid of man and animals. The lactic acid concentration increases in muscle and blood after vigorous activity. L-(+)-Lactic acid is also present in liver, kidney, thymus gland, human amniotic fluid, and o

一般的な説明L-(+)-Lactic acid is the only naturally occurring lactic acid in humans and mammals. Commercially, few bacteria like Lactobacillus casei, L. delbrueckii, Streptococcus lactis produces L-Lactic acid by fermentation process. Lactic acid activates hydroxycarboxylic acid receptor, G-protein coupled receptor 81 (GPR81).

調製方法 · 1 件

純化方法Purify lactic acid by fractional distillation at 0.1mm pressure, followed by fractional crystallisation from diethyl ether/isopropyl ether (1:1, dried with sodium). [Borsook et al. J Biol Chem 102 449 1933.] The solvent mixture, *benzene/diethyl ether (1:1) containing 5% pet ether (b 60-80o) has also been used. [Brin Biochemical Preparations 3 61 1953, Beilstein 3 IV 633.]