trans-4-ヒドロキシ-L-プロリン
L-Hydroxyproline
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基本情報
- CAS
51-35-4- 標準SMILES
O=C(O)[C@@H]1C[C@@H](O)CN1- InChIKey
PMMYEEVYMWASQN-DMTCNVIQSA-N- 分子式
- C5H9NO3
- 平均分子量
- 131.13 g/mol
- 単同位体質量
- 131.05824315
概要
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.
名称と識別子
- 優先名称
- L-Hydroxyproline
- IUPAC
- (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
- 現地名
- trans-4-ヒドロキシ-L-プロリン
- 英語名
- L-Hydroxyproline
- 分子式
- C5H9NO3
- 分子量
- 131.13
名称と別名
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
名称をさらに表示
trans-4-ヒドロキシ-L-プロリン4-ヒドロキシピロリジン-2-カルボン酸(4R)-4-ヒドロキシ-L-プロリン(2S)-4β-ヒドロキシ-2α-ピロリジンカルボン酸4β-ヒドロキシプロリン(2S)-4β-ヒドロキシピロリジン-2α-カルボン酸trans-4-ヒドロキシプロリンL-ヒドロキシプロリン4-ヒドロキシプロリン(2S,4R)-4-ヒドロキシピロリジン-2-カルボン酸2-ヒドロキシプロリン(4R)-4β-ヒドロキシ-L-プロリン4-ヒドロキシ-2-ピロリジンカルボン酸4β-ヒドロキシ-L-プロリン(2S,4R)-4β-ヒドロキシ-L-プロリンヒドロキシプロリンα-ヒドロキシプロリン(4R)-4β-ヒドロキシプロリン(4R)-4-ヒドロキシプロリン(2S,4R)-4-ヒドロキシプロリン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
データベース識別子
- 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
物性
構造計算による物性補完中
- XLogP
- -3.3
- 極性表面積
- 69.6 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 4
- 回転可能結合数
- 1
- 重原子数
- 9
- 形式電荷
- 0
- 複雑度
- 125
実験および物理化学的性質
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
Soluble in water at 0, 25, 50, and 60 °C
361 mg/mL at 25 °C
Boiling PointDecomposes
Melting Point
274°C
274 - 275 °C
Physical Description
Solid; [Merck Index] White crystalline powder; [Alfa Aesar MSDS]
Solid
Dissociation ConstantspK1′ 1.82 and pK2′ 9.65
Collision Cross Section
130.23 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
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.
危険有害性情報
Regulatory Information
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%)
毒性情報
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
化学と産業
薬理情報
Pharmacodynamics
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)
用途と製造
Uses
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
応用分野
解説4-ヒドロキシ-L-プロリン，ヒドロキシプロリン略号Hyp．環状イミノ酸の一つ．非必須アミノ酸trans-ヒドロキシ体の(a)はゼラチン(含量14％)，コラーゲンなどに存在するが，グルタミン酸などからも合成されている．六角板状晶．分解点274 ℃．[α]D－75.6°(水)．pK1 1.92，pK2 9.73，pI5.83．水に易溶，エタノールに微溶．ニンヒドリン呈色は黄色．cis-ヒドロキシ体の(b)はタマゴテングダケの有毒ペプチドphalloidine中に含まれているが，通常のタンパク質中にはない．分解点238～241 ℃．[α]D－58°(水)．これらのN,N-ジメチル誘導体もキブシ科Stachys silvaticaなどの葉や茎に存在している．
説明A non-essential amino acid. Can be isolated from gelatin. Hydroxyproline has not been reported as added to food in any of the NAS surveys.
使用A 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.
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