基本情報
- CAS
474-62-4- 標準SMILES
CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
SGNBVLSWZMBQTH-PODYLUTMSA-N- 分子式
- C28H48O
- 平均分子量
- 400.7 g/mol
- 単同位体質量
- 400.37051615
概要
Campesterol is a 3beta-hydroxy-Delta(5)-steroid, a C28-steroid, a member of phytosterols and a 3beta-sterol. It has a role as a mouse metabolite. It derives from a hydride of a campestane.
名称と識別子
- 優先名称
- Campesterol
- IUPAC
- (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
- 現地名
- カンペステロール
- 英語名
- Campesterol
- 分子式
- C28H48O
- 分子量
- 400.69
名称と別名
CAMPESTEROL474-62-4Campesterin24(R)-methylcholesterolErgost-5-en-3-ol, (3beta,24R)-24alpha-MethylcholesterolErgost-5-en-3beta-ol, (24R)-delta5-24-Isoergosten-3beta-ol(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol5L5O665639CHEBI:28623DTXSID801009891
名称をさらに表示
Δ5-カンペステロールカンペステリン(24R)-24-メチルコレスタ-5-エン-3β-オールエルゴスタ-5-エン-3-オール(24R)-エルゴスタ-5-エン-3β-オール(24R)-24-メチルコレステロールカンペステロール(1R,3aS,3bS,9aR,9bS,11aR)-1-[(2R,5S)-5,6-ジメチルヘプタン-2-イル]-9a,11a-ジメチル-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-7-オール(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,5R)-5,6-ジメチルヘプタン-2-イル]-9a,11a-ジメチル-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-7-オールErgost-5-en-3-ol24α-methyl Cholesterol(24R)-Ergost-5-en-3β-ol
物性
構造計算による物性
- XLogP
- 8.8
- 極性表面積
- 20.2 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 5
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 620
実験および物理化学的性質
Chemical ClassesBiological Agents -> Plant Oils and Extracts
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Ergosterols and C24-methyl derivatives [ST0103]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point157.5 °C
Physical Description
Solid; [Merck Index] White crystalline solid; [Sigma-Aldrich MSDS]
Solid
物理化学的性質
- 融点
- 156 · 156-160 °C
- 比旋光度
- 23 · D23 -33° (22.5 mg in 5 ml chloroform)
- 沸点
- 463.29 °C · 463.29°C (rough estimate)
- 比重(密度)
- 0.98 · 0.98±0.1 g/cm3 (20 ºC 760 Torr)
- 屈折率
- 1.51 · 1.5100 (estimate)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- クロロホルム（少量）、メタノール（少量、超音波処理）
- 酸解離定数(Pka)
- 15.03 · 15.03±0.70(Predicted)
- 外見
- 結晶性
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationChemical: Ergost-5-en-3-ol, (3.beta.,24R)-
Hazards Summary
Phytosterol esters containing 26-29% campesterol demonstrate no significant adverse effects in a 90-day oral study of rats; Phytosterol esters containing 27.9% campesterol produced decreased body weights, increased frequency of cardiomyopathy (males), and changes in hematology parameters in a 13-week oral study of rats at the highest tested dose (9,000 mg/kg/day); Phytosterol esters show no evidence of reproductive or developmental toxicity in rats; [JECFA] A moderate irritant; Harmful by ingestion, inhalation, and skin absorption; Targets the eyes, kidney, liver, and heart; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
安全データ
- wgk
- 3
- ridadr
- UN 1888 6.1/PG 3
- hs_code
- 29061990
- risk_code
- 20/21/22-36/37/38-48/20/22-40-38-22
- hazard_code
- Xn,T
- safety_code
- 26-36-45-36/37/39-23
- Hazard Classifications
化学と産業
薬理情報
Tissue LocationsKidney
Cellular LocationsExtracellular
用途と製造
UsesPresent in rape-seed oil, soybean oil, and wheat germ oil; [Merck Index] Added to food as a source of phytosterols (for blood cholesterol lowering properties); [JECFA]
応用分野
解説カンペステロール，(3β,24R)-ergost-5-ene-3-ol．C28H48O(400.69)．西洋アブラナの種子，大豆油，小麦胚芽，ナタネ，海藻などに含まれるステロイドアルコール．24-メチレンコレステロールの還元によっても得られる．無色の結晶．融点157～158 ℃．[α]23D－33°(クロロホルム)．クロロホルム，ベンゼン，エーテルに易溶．
説明24α-methyl Cholesterol is a phytosterol found in vegetables, fruits, nuts, and seeds that competitively inhibits the absorption of intestinal cholesterol and decreases the transcription of genes important for cholesterol metabolism. The cholesterol lowering effects of phytosterols, such as 24α-methyl cholesterol, have been reported to be beneficial for lowering the incidence of atherosclerotic plaques. 24α-methyl Cholesterol can also act as an agonist at liver X receptors (LXR) and, through activation of LXR signaling, has been shown to suppress the proliferation of prostate and breast cancer cells.
使用Campesterol may be used as a plant sterol to test its effect on the transcriptional activation of liver X receptor α (LXRA) in breast cancer cells. It may also be used as a sterol standard for calibration curve generation in liquid chromatography multiple reaction monitoring (LC-MRM) analysis.
一般的な説明Campesterol is a plant sterol, which is an analog of cholesterol and a brassinosteroid (BR) precursor. The enzyme diminute/dwarf1 mediates the synthesis of campesterol from 24-methylenecholesterol. Campesterol possesses methyl group at C-24 position of the side chain in the cholesterol structure.
調製方法
関連反応
1 件
化合物ノート
読み込み中…