하이드록시프롤린

L-Hydroxyproline

HCID 5810CAS 51-35-4
부분 구조 검색유사 구조 찾기

기본 정보

표준 SMILES
O=C(O)[C@@H]1C[C@@H](O)CN1
InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N
분자식
C5H9NO3
평균 분자량
131.13 g/mol
단동위원소 질량
131.05824315

개요

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.

이름 및 식별자

우선 이름
L-Hydroxyproline
IUPAC
(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
현지명
하이드록시프롤린
영어명
L-Hydroxyproline
분자식
C5H9NO3
분자량
131.13

이름 및 동의어

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
이름 더 보기
하이드록시프롤린4-하이드록시프롤린Hyp(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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-3.3
극성 표면적
69.6 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
4
회전 가능 결합 수
1
무거운 원자 수
9

실험 및 물리화학적 성질

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 · 2건

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

361 mg/mL at 25 °C

물리화학적 성질

녹는점
273 °C · 273 °C (dec.)(lit.)
끓는 점
242.42 °C · 242.42°C (rough estimate)
밀도
1.3121 · 1.3121 (rough estimate)
증기 밀도
4.5 · 4.5 (vs air)
굴절률
-75.5 ° · -75.5 ° (C=4, H2O)
저장 조건
30 °C · Store below +30°C.

화학적 성질

White crystalline powder

안전 및 규제

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 3건

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%)

독성 정보

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

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
TW3586500
HS 번호
29339990
risk_code
36/37/38-22
hazard_code
Xi,Xn

화학 및 산업

약리 정보

Pharmacodynamics · 1건

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)

용도 및 제조

Uses · 2건

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
응용 분야 · 3건

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

용도A 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.

일반 설명Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

제조 방법 · 1건

생산 방법In the past L-Hydroxyproline was isolated by hydrolysis of animal collagen, e. g. gelatine or collagen, of which it is a major constituent. L-Hydroxyproline is an unnatural amino acid which is made in the body by hydroxylation of L-Proline. The presence of L-Hydroxyproline and proline are key to maintaining the stability of the tight collagen helix. Today L-Hydroxyproline is manufactured by bio-catalysed hydroxylation of proline in bacteria. Together with its other isomers, L-Hydroxyproline is also used as an inter mediate for a range of pharmaceutical active ingredients. Produced by hydroxylation of L-proline after protein synthesis. It is contained rich in collagen and elastin. Known to stabilization of triple-helix structure of collagen. Widely used as an intermediate for medicines.

상·하류 제품 정보

공급사50 곳

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]

추가 설명

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

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