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하이드록시프롤린

trans-hydroxy-L-proline

HCID 6971053
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
51-35-4
표준 SMILES
O=C([O-])[C@@H]1C[C@@H](O)C[NH2+]1
InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N
분자식
C5H9NO3
평균 분자량
131.13 g/mol
단동위원소 질량
131.05824315

개요

Trans-4-hydroxy-L-proline zwitterion is an L-alpha-amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of trans-4-hydroxy-L-proline; major species at pH 7.3. It is a tautomer of a trans-4-hydroxy-L-proline.

이름 및 식별자

우선 이름
trans-hydroxy-L-proline
IUPAC
(2S,4R)-4-hydroxypyrrolidin-1-ium-2-carboxylate
현지명
하이드록시프롤린
영어명
L-Hydroxyproline
분자식
C5H9NO3
분자량
131.13

이름 및 동의어

trans-oxyprolinetrans-hydroxy-L-prolinehydroxyproline zwitteriontrans-L-4-hydroxy-prolineCHEBI:58375trans-4-hydroxy-L-proline zwitterion하이드록시프롤린4-하이드록시프롤린HypTRANS-4-HYDROXY-L-PROLINEHYDROXYPROLINE(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
이름 더 보기
4-HYDROXY-L-PROLINE4-HydroxyprolineH-HYP-OH4R-4-hydroxyproline4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID5kg

데이터베이스 식별자

CAS
51-35-4、618-28-0
PubChem CID
6971053
ChEBI
CHEBI:58375

물성

구조 계산 물성

XLogP
-2.7
극성 표면적
77 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
0
무거운 원자 수
9
형식 전하
0
복잡도
120

실험 및 물리화학적 성질

LogP-3.17
Solubility · 2건

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

361 mg/mL at 25 °C

Boiling PointDecomposes
Melting Point · 2건

274°C

274 - 275 °C

Physical DescriptionSolid
Dissociation ConstantspK1′ 1.82 and pK2′ 9.65

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.
용해도
2 O: · H2O: 50 mg/mL
물리적 상태
결정 또는 결정성 분말
산도 계수 (pKa)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
TW3586500
HS 번호
29339990
risk_code
36/37/38-22
hazard_code
Xi,Xn
safety_code
24/25-36/37/39-27-26
위험 등급
IRRITANT
스토리지 클래스
11 - Combustible Solids

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)
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.

관련 반응

0건
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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
1.82 · 1.82, 9.66(at 25℃)
색상
하얀색
냄새
냄새 없는
수소이온지수(pH)
5.5 · 5.5-6.5 (50g/l, H2O, 20℃)
수용성
357.8 g/L · 357.8g/L(20℃)
Merck
14 · 14,4840
BRN
471933 · 471933
화장품 원료 기능
헤어 컨디셔닝대전방지제계면활성제 - 세정피부 컨디셔닝
InChI
1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N
SMILES
O[C@H]1CN[C@@H](C1)C(O)=O
LogP
-0.35 · -0.350 (est)
NIST
Hydroxyproline(51-35-4)
EPA
-4 · trans-4-Hydroxy-L-proline (51-35-4)

화학적 성질

White crystalline powder

상·하류 제품 정보

상류 원료

Soy bean Isoflavone Isoflavone 10-40%Α-proteinBone glue카세인젤라틴

하류 제품

N-Boc-cis-4-Hydroxy-L-proline methyl ester(R)-(-)-3-Pyrrolidinol hydrochloride(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidinetert-부틸2,5-디아자비시클로[2.2.1]헵탄-2-카르복실레이트염산염N-Boc-4-oxo-L-Proline methyl esterFmoc-L-하이드록시프롤린3-[[[(2S,4S)-4-Mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid1-Boc-2-하이드록시메틸-4-M…2-피롤리딘메탄올,4-하이드록시-,염산염(1:1),(2S,4R)-BETONICINE트랜스-4-하이드록시-1-(4-니트로벤질일록시카르보닐)-L-프롤린N-Cbz-cis-4-hydroxy-D-proline methyl ester1-벤질피롤1-페닐피롤

공급사100 곳

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추가 설명

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