L-Serine

HCID 5951CAS 302-84-1

Grundinformationen

Standard-SMILES
N[C@@H](CO)C(=O)O
InChIKey
MTCFGRXMJLQNBG-REOHCLBHSA-N
Summenformel
C3H7NO3
Durchschnittliche Molmasse
105,09 g/mol
Monoisotopische Masse
105,04259308

Überblick

L-serine is the L-enantiomer of serine. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a human metabolite and an algal metabolite. It is a L-alpha-amino acid, a serine, a serine family amino acid and a proteinogenic amino acid. It is a conjugate base of a L-serinium. It is a conjugate acid of a L-serinate. It is an enantiomer of a D-serine. It is a tautomer of a L-serine zwitterion.

Namen und Bezeichner

Bevorzugter Name
L-Serine
IUPAC
(2S)-2-amino-3-hydroxypropanoic acid
Englischer Name
(2S)-2-amino-3-hydroxy-propanoic acid
Summenformel
C3H7NO3
Molmasse
0

Namen und Synonyme

L-serineserine56-45-1(S)-2-Amino-3-hydroxypropanoic acid(S)-Serinebeta-HydroxyalanineL-(-)-SerineL-ser(2S)-2-amino-3-hydroxypropanoic acidSerinaL-SerinSER (IUPAC abbrev)
Weitere Namen anzeigen
L-SERINE FBrn 1721404L-SERINE F, USPCysteine Impurity BCysteine hydrochloride EP Impurity B2-Amino-3-hydroxypropanoic acid, (S)-(2S)-2-amino-3-hydroxy-propanoic acid
Serinumalpha-Amino-beta-hydroxypropionic acidSereneL-3-Hydroxy-alaninebeta-Hydroxy-L-alanineL-2-Amino-3-hydroxypropionic acidL-3-Hydroxy-2-aminopropionic acidPropanoic acid, 2-amino-3-hydroxy-, (S)-

Datenbank-Bezeichner

CAS
302-84-1、56-45-1、6898-95-9
PubChem CID
5951
DTXSID
DTXSID301031857
ChEMBL
CHEMBL11298
ChEBI
CHEBI:17115
UNII
452VLY9402
EC Number
200-274-3、630-352-6
Nikkaji
J1.195I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-3,1
Polarare Oberfläche (TPSA)
83,6 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
2
Schwere Atome
7

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 2 Einträge

Cosmetic ingredients (Serine) -> CIR (Cosmetic Ingredient Review)

Hair conditioning; Antistatic; Skin conditioning

LogP · 2 Einträge

LogP = -3.07

-3.07

Taste · 2 Einträge

SWEETISH TASTE, INSIPID AFTERTASTE

Sweet

Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

This chemical does not meet GHS hazard criteria for 94% (236 of 251) of all reports.

Not Classified

Aggregated GHS information provided per 251 reports by companies from 6 notifications to the ECHA C&L Inventory.

Not Classified

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: L-Serine

Status: Active Update: 07-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5558

Serine: Does not have an individual approval but may be used under an appropriate group standard

L-serine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - L-Serine: Environment tier I assessment
Hazards SummaryDoes not appear to reach the fetus of pregnant pigs (placenta metabolizes to glycine); Small increase in resorptions observed in rats following intraperitoneal treatment; [REPROTOX]
FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Hazard Classes and Categories · 2 Einträge

Not Classified

Not Classified

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, 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

INTRACEREBROVENTRICULAR INJECTIONS OF ALANINE (0.5-2.0 UG) INTO RABBITS CAUSED DECR IN BODY TEMP IN A 10-DEG ENVIRONMENT. THE EFFECT WAS SLIGHTLY SUBADDITIVE WITH THAT OF SERINE.

ERYTHROBLASTIC LEUKEMIC CELLS INCUBATED IN MEDIA CONTAINING ESSENTIAL AMINO ACID L-SERINE BOUND APPROX 30% MORE INSULIN LABELED WITH (125)IODINE THAN THOSE INCUBATED WITHOUT SERINE.

Toxicity Summary · 2 Einträge

Safe 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

L-Serine plays a role in cell growth and development (cellular proliferation). The conversion of L-serine to glycine by serine hydroxymethyltransferase results in the formation of the one-carbon units necessary for the synthesis of the purine bases, adenine and guanine. These bases when linked to the phosphate ester of pentose sugars are essential components of DNA and RNA and the end products of energy producing metabolic pathways, ATP and GTP. In addition, L-serine conversion to glycine via this same enzyme provides the one-carbon units necessary for production of the pyrimidine nucleotide, deoxythymidine monophosphate, also an essential component of DNA.

Natural Pollution SourcesNATURALLY OCCURRING FORM IS L-SERINE.
Human Toxicity Excerpts · 2 Einträge

HUMAN NEUROBLASTOMA SK-N-SH-SY5Y (5Y) CELLS WERE CULTURED WITH SUPPLEMENTAL SERINE FOR 3-6 DAYS. SERINE HYDROXYMETHYLTRANSFERASE WAS ASSAYED. NO CHANGES IN SPECIFIC ACTIVITY OR CELLULAR MORPHOLOGY WERE NOTED @ CONCN LESS THAN 16 UMOL.

METABOLIC EFFECTS OF CONTROLLED MODIFIED INTAKES OF L-SERINE IN PARENTERAL NUTRITION SOLUTIONS WERE INVESTIGATED IN NORMAL ADULTS.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 4 Einträge

ADMIN TO RATS ON DAYS 8-14 OF PREGNANCY, VARIOUS AMINO ACIDS INCL SERINE INCR % RESORPTIONS FROM CONTROL VALUE OF 1.85% TO 5.36-8.85%. ADMIN IP AT 0.1 ML 0.3 MOLAR SOLN/DAY.

RAT GLIOMA CELLS (C6) CULTURED WITH SUPPLEMENTAL SERINE FOR 3-6 DAYS. SERINE HYDROXYMETHYLTRANSFERASE WAS ASSAYED. NO CHANGES IN SPECIFIC ACTIVITY OR CELLULAR MORPHOLOGY NOTED @ CONCN LESS THAN 16 UMOL. CONCN OF 20 AND 40 UMOL LED TO LOWER GLIOMAL ENZYME SPECIFIC ACTIVITIES.

THE GROWTH OF RABBIT HAIR WAS STIMULATED BY L-SERINE.

SERINE INCREASED ETHANOL CONSUMPTION IN ISOLATED HEPATOCYTES FROM 18-HR STARVED AND FED RATS.

Regulatorische Informationen

FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Chemie und Industrie

Pharmakologische Informationen

Bionecessity · 2 Einträge

AMINO ACID CLASSED AS NONESSENTIAL FOR MAINTENANCE OF GROWTH IN RATS.

SERINE WAS ESSENTIAL FOR OPTIMAL GROWTH OF EMBRYONIC RAT CELLS IN TISSUE CULTURE. SERINE CAN BE REPLACED BY GLYOXYLIC ACID BUT NOT BY GLYCINE OR GLYCOLIC ACID.

Pharmacodynamics · 1 Eintrag

Serine is classified as a nutritionally non-essential amino acid. Serine is critical for the production of the body's proteins, enzymes and muscle tissue. Serine is needed for the proper metabolism of fats and fatty acids. It also helps in the production of antibodies. Serine is used as a natural moisturizing agent in some cosmetics and skin care products. The main source of essential amino acids is from the diet, non-essential amino acids are normally synthesize by humans and other mammals from common intermediates.

Mechanism of Action · 1 Eintrag

L-Serine plays a role in cell growth and development (cellular proliferation). The conversion of L-serine to glycine by serine hydroxymethyltransferase results in the formation of the one-carbon units necessary for the synthesis of the purine bases, adenine and guanine. These bases when linked to the phosphate ester of pentose sugars are essential components of DNA and RNA and the end products of energy producing metabolic pathways, ATP and GTP. In addition, L-serine conversion to glycine via this same enzyme provides the one-carbon units necessary for production of the pyrimidine nucleotide, deoxythymidine monophosphate, also an essential component of DNA.

Absorption, Distribution and Excretion · 4 Einträge

IN PT AGE 2-9 YR, SERINE PRESENT IN ACID MUCOPOLYSACCHARIDES. EXCESSIVE ACCUMULATION & EXCRETION IN URINE OF MUCOPOLYSACCHARIDES MAY BE RELATED TO ABNORMAL BONDING BETWEEN MUCOPOLYSACCHARIDES & PROTEIN.

IN PT AGE 2-9 YR, URINARY SERINE EXCRETION INCR FROM 0.059-0.162 UMOL/24 HR & PLASMA SERINE LEVELS INCR FROM 0.102-0.158 UMOL/ML.

IN PT AGE 2-9 YR, SERINE IS PROBABLY NOT ESTERIFIED THROUGH ITS BETA-HYDROXYL GROUP TO ACID MUCOPOLYSACCHARIDES BUT IS LINKED BY CARBOXYL GROUP.

DETERMINATION OF SERINE LEVELS IN 13 REGIONS OF THE RAT CEREBRAL CORTEX FAILED TO SHOW ANY MARKED DIFFERENCES IN THE AMINO ACID CONTENTS OF CORTEX AREAS OF DIVERSE FUNCTIONS.

Tissue LocationsAll Tissues
Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Serine

Non-essential amino acid; [Merck Index] Used in parenteral nutrition, biomedical research, culture media, microbiological tests, feed additives, and skin care creams; [HSDB] Used as a flavoring agent and nutritional supplement for foods; [FDA]

Farming (Feed Additives) [Category: Industry]

Medical use: parenteral nutrition, dietary supplement

IN BIOCHEMICAL RESEARCH, CULTURE MEDIA, MICROBIOLOGICAL TESTS; FEED ADDITIVE; DIETARY SUPPLEMENT

Cosmetics: serine is one component of skin care cream or lotions

U.S. ProductionWorld market for L-serine in 1982: 50 tonnes
Methods of Manufacturing · 3 Einträge

ISOLATED FROM SILK FIBROIN (SERICINE)

Production methods for L-serine include extraction and fermentation; extraction of hydrolysates and fermentation of glycine substrate are the preferred methods for producing L-serine... microorganisms suggested for the fermentation production of L-serine from glycine include mutants of the genera Pseudomonas, Corynebacterium glycinophilum, and Norcardia

Hydrolysis of protein (especially silk protein); synthesized from glycine

Formulations/PreparationsFlavor, food and pharmaceutical grades; USP and FCC grades
Household ProductsInformation on 36 consumer products that contain Serine in the following categories is provided:
Use ClassificationCosmetics -> Hair conditioning; Antistatic; Skin conditioning

Anbieter3 Anbieter

深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
陕西缔都医药化工有限公司+86-29-87569262 +86-15003564040 · [email protected]
常州翔龙医药科技有限公司18661161657 · [email protected]

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