L-4-Hydroxyprolin

L-Hydroxyproline

HCID 5810CAS 51-35-4
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Grundinformationen

Standard-SMILES
O=C(O)[C@@H]1C[C@@H](O)CN1
InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N
Summenformel
C5H9NO3
Durchschnittliche Molmasse
131,13 g/mol
Monoisotopische Masse
131,05824315

Überblick

Trans-4-hydroxy-L-proline is an optically active form of 4-hydroxyproline having L-trans-configuration. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is a tautomer of a trans-4-hydroxy-L-proline zwitterion.

Namen und Bezeichner

Bevorzugter Name
L-Hydroxyproline
IUPAC
(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
Lokaler Name
L-4-Hydroxyprolin
Englischer Name
L-Hydroxyproline
Summenformel
C5H9NO3
Molmasse
131.13

Namen und Synonyme

L-Hydroxyproline51-35-4trans-4-Hydroxy-L-prolinehydroxyprolineHyprohydroxy-L-proline(4R)-4-hydroxy-L-prolinetrans-L-HydroxyprolineL-Proline, 4-hydroxy-, (4R)-trans-Hydroxyproline4-Hydroxy-2-pyrrolidinecarboxylic aciddelta-Hydroxyproline
Weitere Namen anzeigen
Hyp(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID4-HYDROXY-L-PROLINE4-HydroxyprolineH-HYP-OH4R-4-hydroxyproline4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID5kg
L-Proline, 4-hydroxy-, trans-(2S,4R)-4-hydroxyprolineRMB44WO89XLUMISTORL-threo-4-hydroxyprolineNSC-46704(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acidCHEBI:18095

Datenbank-Bezeichner

CAS
51-35-4、618-28-0
PubChem CID
5810
DTXSID
DTXSID10883225
ChEMBL
CHEMBL352418
ChEBI
CHEBI:18095
UNII
RMB44WO89X
EC Number
200-091-9
Nikkaji
J148.015D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-3,3
Polarare Oberfläche (TPSA)
69,6 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
1
Schwere Atome
9

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning; Surfactant; Antistatic; Hair conditioning
LogP-3.17
Food AdditivesUse unspecified -> FDA Substance added to food
Solubility · 2 Einträge

Soluble in water at 0, 25, 50, and 60 °C

361 mg/mL at 25 °C

Physikochemische Eigenschaften

Schmelzpunkt
273 °C · 273 °C (dec.)(lit.)
Siedepunkt
242.42 °C · 242.42°C (rough estimate)
Dichte
1.3121 · 1.3121 (rough estimate)
Dampfdichte
4.5 · 4.5 (vs air)
Brechungsindex
-75.5 ° · -75.5 ° (C=4, H2O)
storage temp.
30 °C · Store below +30°C.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 89.3% (25 of 28) of all reports.

Warning

H315 (10.7%): 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 28 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: L-Proline, 4-hydroxy-, (4R)-

Status: Active Update: 27-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21207

L-Proline, 4-hydroxy-, (4R)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - L-Proline, 4-hydroxy-, trans-: Environment tier I assessment
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See L-Proline.
Hazard Classes and CategoriesSkin Irrit. 2 (10.7%)

Toxikologische Informationen

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29339990
RTECS-Nr.
TW3586500
risk_code
36/37/38-22
hazard_code
Xi,Xn

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

Hydroxyproline as well as proline and glycine are the major components of collagen. Collagen is on one of the main building blocks of connective tissue such as skin, bone, and cartilage. Thus when these tissues are damaged, hydroxyproline is necessary for repair of the damaged area.

Tissue LocationsEpidermis
Cellular LocationsEndoplasmic reticulum
Metabolite PathwaysArginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)

Verwendung und Herstellung

Uses · 2 Einträge

An analog of proline and an non-essential amino acid found in collagen; [Merck Index]

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

Use ClassificationCosmetics -> Skin conditioning; Surfactant; Antistatic; Hair conditioning
General Manufacturing InformationL-Proline, 4-hydroxy-, (4R)-: ACTIVE
Anwendungen · 2 Einträge

BeschreibungA non-essential amino acid. Can be isolated from gelatin. Hydroxyproline has not been reported as added to food in any of the NAS surveys.

VerwendenA natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
苏州华赛生物工程技术有限公司0512-89581819; 18915732708 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An optically active form of 4-hydroxyproline having L-trans-configuration.

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