(+)-4-コレステン-3-オン

Cholest-4-en-3-one

HCID 91477
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基本情報

CAS
601-57-0
標準SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
NYOXRYYXRWJDKP-GYKMGIIDSA-N
分子式
C27H44O
平均分子量
384.6 g/mol
単同位体質量
384.33921603

概要

Cholest-4-en-3-one is a cholestanoid that is cholest-4-ene substituted by an oxo group at position 3. It has a role as a plant metabolite and a human metabolite. It is a 3-oxo-Delta(4) steroid and a cholestanoid.

名称と識別子

優先名称
Cholest-4-en-3-one
IUPAC
(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
現地名
(+)-4-コレステン-3-オン
英語名
4-Cholesten-3-one
分子式
C27H44O
分子量
384.64

名称と別名

4-Cholesten-3-oneCholestenone601-57-0cholest-4-en-3-one3-Oxocholest-4-ene7T94NHD99CDTXSID90872379CHEBI:16175NSC-63000NSC-134926(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-3-one
名称をさらに表示
(+)-4-コレステン-3-オンコレステノン4-コレステン-3-オンΔ4-コレステノンコレスタン-4-エン-3-オンコレスタ-4-エン-3-オン(20R)-コレスタ-4-エン-3-オンコレステロン(+)-3-オキソ-4-コレステンΔ4-コレステン-3-オン(+)-コレステン-3-オン(1R,3aS,3bS,9aR,9bS,11aR)-9a,11a-ジメチル-1-[(2R)-6-メチルヘプタン-2-イル]-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-7-オン3-オキソコレスタ-4-エン4-Cholestenone4-Cholestene-3-oneCHOLEST-4-ENE-3-ONE
RefChem:576025DTXCID40820027210-005-1Cholesterone(+)-4-Cholesten-3-one3-Oxo-4-cholestene3-Keto-4-cholestenedelta(sup 4)-Cholestenone

データベース識別子

CAS
601-57-0
PubChem CID
91477
DTXSID
DTXSID90872379
ChEMBL
CHEMBL63243
ChEBI
CHEBI:16175
UNII
7T94NHD99C
EC Number
210-005-1
Nikkaji
J73F

物性

構造計算による物性

XLogP
8.4
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
5
重原子数
28

実験および物理化学的性質

LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
SpringerMaterials PropertiesCrystal structure
Melting Point79 - 82 °C
Physical DescriptionSolid

物理化学的性質

融点
79 · 79-82 °C
比旋光度
92.5 · 92.5 º (c=2, CHCl3)
沸点
451.27 °C · 451.27°C (rough estimate)
比重(密度)
0.9717 · 0.9717 (rough estimate)
屈折率
1.51 · 1.5100 (estimate)
貯蔵温度
-20 °C · -20°C

化学的性質

化学的特性white to light yellow crystals or powder

安全と法規制

GHS分類

GHS Classification · 3 件

H413 (95%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAquatic Chronic 4 (95%)

安全データ

wgk
3
tsca
TSCA listed
rtecs
FZ7700000
hs_code
29142900
risk_code
36/37/38
hazard_code
Xi

化学と産業

薬理情報

Tissue LocationsGall Bladder
Cellular LocationsExtracellular

用途と製造

General Manufacturing InformationCholest-4-en-3-one: ACTIVE
応用分野 · 3 件

説明Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol. It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 μg/ml. Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland. It has been used as synthetic intermediate in the synthesis of steroids.

使用4-Cholesten-3-one is used as a chiral building block for proteomics research. It is an intestinal metabolite of cholesterol and exhibits an anti-obesity effect on animals.

一般的な説明Cholestenone is a cholesterol metabolite and analog, which substitutes membrane cholesterol and elevates membrane fluidity.

上流・下流製品情報

サプライヤー100 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

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