基本情報
- CAS
57-91-0- 標準SMILES
C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@H]2O- InChIKey
VOXZDWNPVJITMN-SFFUCWETSA-N- 分子式
- C18H24O2
- 平均分子量
- 272.4 g/mol
- 単同位体質量
- 272.17763
概要
17alpha-estradiol is an estradiol that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17 (the 17alpha stereoisomer). It has a role as a geroprotector and an estrogen. It is an estradiol, a 17alpha-hydroxy steroid and a 3-hydroxy steroid.
名称と識別子
- 優先名称
- alpha-Estradiol
- IUPAC
- (8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
- 現地名
- アルファトラジオール
- 英語名
- Estradiol
- 分子式
- C18H24O2
- 分子量
- 272.39
名称と別名
17alpha-Estradiol57-91-0alpha-EstradiolAlfatradiol17a-estradiol17-alpha-EstradiolEstradiol-17alpha3,17-DihydroxyestratrieneEpiestrol17-Epiestradiol(8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diolDTXSID8022377
名称をさらに表示
エストラ-1,3,5(10)-トリエン-3,17α-ジオールエピエストラジオールα-エストラジオール17α-エストラジオール17-α-エストラジオール1,3,5(10)-エストラトリエン-3,17α-ジオールエストラ-1(10),2,4-トリエン-3,17α-ジオールエストラジオール-17α17Α-エストラジオール標準品17Α‐エストラジオール標準品Α-エストラジオール17Α-エストラジオールアルファトラジオール(1R,3aS,3bR,9bS,11aS)-11a-メチル-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-1,7-ジオールα-EstradiolBETA-ESTRADIOL17B-ESTRADIOLB-ESTRADIOL17α-estradiolEPIESTRADIOL
ESTRADIOL, ALPHA-3VQ38D63M7DTXCID702377Oestra-1,3,5(10)-triene-3,17alpha-diolCHEBI:171603,17alpha-Dihydroxyestra-1,3,5(10)-triene3,17alpha-Dihydroxyoestra-1,3,5(10)-trienealfatradiolum
物性
構造計算による物性
- XLogP
- 4
- 極性表面積
- 40.5 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 2
- 回転可能結合数
- 0
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 382
実験および物理化学的性質
Chemical ClassesHormone
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C18 steroids (estrogens) and derivatives [ST0201]
SpringerMaterials PropertiesAngular frequency
Solubility0.0039 mg/mL
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point216 - 219 °C
Physical DescriptionSolid
Collision Cross Section174.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID8022377]
物理化学的性質
- 融点
- 176 · 176-180 °C(lit.)
- 比旋光度
- 20 · D20 +53 to +56° (c = 0.9 in dioxane)
- 沸点
- 355.44 °C · 355.44°C (rough estimate)
- 比重(密度)
- 1.0708 · 1.0708 (rough estimate)
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 1.9% (3 of 154) of reports.
Danger
H350 (11.7%): May cause cancer [Danger Carcinogenicity]
P203, P260, P263, P264, P270, P280, P318, P319, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 154 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory InformationEstra-1,3,5(10)-triene-3,17-diol, (17.alpha.)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesCarc. 1A (11.7%)
毒性情報
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
USGS Health-Based Screening Levels for Evaluating Water-Quality
17-alpha-Estradiol
Hormone
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
安全データ
- F
- 8-10
- wgk
- 3
- rtecs
- KG3750000
- ridadr
- UN 2811 6.1/PG 2
- hs_code
- 29372390
- risk_code
- 45-48-40
化学と産業
薬理情報
Mechanism of Action
MITO-4509 is an orally-administered drug candidate that shows neuro-protective activity and reductions in beta-amyloid in animal models of Alzheimer's disease, and is well tolerated in a completed human Phase I trial. In addition to Alzheimer's disease, MITO-4509 shows potential for use in Parkinson's disease, Friedreich's ataxia, retinitis pigmentosa, and mild cognitive impairment ("MCI" is often considered a precursor to Alzheimer's disease).
MeSH Pharmacological Classification
Drugs used to treat or prevent skin disorders or for the routine care of skin.
Drugs that inhibit 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE. They are commonly used to reduce the production of DIHYDROTESTOSTERONE.
Cellular LocationsExtracellular
用途と製造
UsesUse (kg; approx.) in Germany (2009): >10
応用分野
用途薬理・生理作用研究用。
使用Estradiol (known as α-Estradiol or 17 α-Estradiol) is a biologically active estrogen in human breast cancer cells in tissue culture. 17-Εstradiol and its selective receptor, ER-X, are not part of a classical hormone/receptor endocrine system but of a system with important autocrine/paracrine functions in the developing and adult brain. 17-Estradiol may have enormous implications for hormone replacement strategies at the menopause and in the treatment of such neurodegenerative disorders as Alzheimer’s disease and ischemic stroke.
調製方法
純化方法17-Estradiol recrystallises from aqueous EtOH (80%) as the hemihydrate and differs from the -anomer (below) by not precipitating with digitonin in 80% aqueous EtOH. The diacetate [1474-52-8] crystallises from aqueous EtOH in needles with m 139-140o. The 3-benzoate crystallises in three forms m 158o, 153o and 63o.
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