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l-(+)-Milchsaeure

L-Lactic Acid

HCID 107689
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Grundinformationen

CAS
79-33-4
Standard-SMILES
C[C@H](O)C(=O)O
InChIKey
JVTAAEKCZFNVCJ-REOHCLBHSA-N
Summenformel
C3H6O3
Durchschnittliche Molmasse
90,08 g/mol
Monoisotopische Masse
90,03169405

Überblick

(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.

Namen und Bezeichner

Bevorzugter Name
L-Lactic Acid
IUPAC
(2S)-2-hydroxypropanoic acid
Lokaler Name
l-(+)-Milchsaeure
Englischer Name
L(+)-Lactic acid
Summenformel
C3H6O3
Molmasse
90.08

Namen und Synonyme

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 acidLactic acid, L-Tisulac
Weitere Namen anzeigen
2-HYDROXYPROPIONIC ACIDLACTIC ACIph90EspiritinHiPure 90PURAC(R) 50
(S)-(+)-Lactic acidPropanoic acid, 2-hydroxy-, (2S)-Sarcolacticum acidumL-(+)-alpha-Hydroxypropionic acidF9S9FFU82NCHEBI:422DTXSID6034689Lactisan Winter

Datenbank-Bezeichner

CAS
79-33-4
PubChem CID
107689
DTXSID
DTXSID6034689
ChEMBL
CHEMBL330546
ChEBI
CHEBI:422
UNII
F9S9FFU82N

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-0,7
Polarare Oberfläche (TPSA)
57,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
6
Formalladung
0
Komplexität
59,1

Experimentelle und physikochemische Eigenschaften

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 Einträge

Liquid

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

Liquid

Dissociation Constants3.861

Physikochemische Eigenschaften

Schmelzpunkt
52 · 52-54°C
Siedepunkt
125 °C · 125 °C

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 · 6 Einträge

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]

Gefahrenhinweise

Regulatory Information · 4 Einträge

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)

REACH registered substance: L-(+)-lactic acid (EC: 201-196-2)

(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 Eintrag

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

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Metabolite PathwaysFructose-1,6-diphosphatase deficiency

Verwendung und Herstellung

Uses · 3 Einträge

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 Einträge

Zugehörige Reaktionen

177
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Reaktionsgleichung von HRID 31001
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Reaktionsgleichung von HRID 31020
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Reaktionsgleichung von HRID 241828
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EC Number
201-196-2
Nikkaji
J9.134K
Dichte
1.206 g/mL · 1.206 g/mL at 25 °C
Dampfdruck
0.038 Pa · 0.038Pa at 25℃
FEMA
2611 · 2611 | LACTIC ACID
Brechungsindex
20 · n20/D 1.427
Flammpunkt
230 °F · >230 °F
storage temp.
2 · 2-8°C
Löslichkeit
2 O: · H2O: 10 mg/mL, clear, colorless
Aggregatzustand
Powder/Solid
pka
25 °, · pK at 25°, 3.79
Farbe
White
Geruch (Odor)
odorless acidic
PH
2.8 · 2.8 (20°C, 10g/L in H2O)
Geruchsart
odorless
Wasserlöslichkeit
SOLUBLE
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 Datenbank
79 · 79-33-4(CAS DataBase Reference)
NIST chemische Informationen
-2 · (s)-2-Hydroxypropanoic acid(79-33-4)
EPA chemische Informationen
L-Lactic acid (79-33-4)
Hazard Classes and Categories · 5 Einträge

Skin Corr. 1C (36.1%)

Skin irritation - category 2

Skin corrosion/irritation - Category 1

Skin corrosion/irritation - Category 1

Skin Corr. 1C

Toxikologische Informationen

Health Effects · 1 Eintrag

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 Eintrag

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 Einträge

Not listed by IARC.

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

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

Sicherheitsdaten

F
3-10
wgk
1
tsca
TSCA listed
ridadr
3261
hs_code
29181100
RTECS-Nr.
OD2800000
risk_code
38-41-34-36/37/38-36-35
Toxizität
LD50 intraperitoneal in mouse: 3194mg/kg
hazard_code
Xi,C
safety_code
26-39-45-36/37/39-36
hazard_class
8
packing_group
III
Speicherklasse
8A - Combustible corrosive hazardous materials
Hazard Classifications
Eye Dam. 1Skin Corr. 1C

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

General Manufacturing Information · 2 Einträge

Wholesale and Retail Trade

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

Anwendungen · 1 Eintrag

VerwendenOccurs 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

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Strke

Nachgelagerte Produkte

Lithium-(S)-lactatNatrium-(S)-lactatNatriumlactatCarbetamidMethanolEthyl-2-[4-[(6-chlorbenzoxazol-2-yl)oxy]phenoxy]propionatQuizalofop-p-ethylCalciumdilactat(S)-1-[4-[[2-(2-Aminopyrimidin-5-yl)-7-methyl-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one

Ergänzende Hinweise

DefinitionChEBI: An optically active form of lactic acid having (S)-configuration.