Pregna-4,16-dien-3,20-dion

Pregna-4,16-diene-3,20-dione

HCID 101964CAS 1096-38-4

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Grundinformationen

Standard-SMILES: CC(=O)C1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey: VRRHHTISESGZFN-RKFFNLMFSA-N
Summenformel: C21H28O2
Durchschnittliche Molmasse: 312,4 g/mol
Monoisotopische Masse: 312,20893014

Überblick

16,17-didehydroprogesterone is a 20-oxo steroid, a 3-oxo-Delta(4) steroid and an enone. It is functionally related to a progesterone.

Namen und Bezeichner

Bevorzugter Name: Pregna-4,16-diene-3,20-dione
IUPAC: (8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
Lokaler Name: Pregna-4,16-dien-3,20-dion
Englischer Name: 16-Dehydroprogesterone
Summenformel: C21H28O2
Molmasse: 312.45

Namen und Synonyme

16-Dehydroprogesterone1096-38-4Pregna-4,16-diene-3,20-dione16,17-Didehydroprogesterone3,20-Dioxopregna-4,16-dieneJU0YQ9DZ2ONSC-11037NSC-9785Delta(4,16)-pregnadiene-3,20-dioneCHEBI:18204DTXSID10862535RefChem:78965

Weitere Namen anzeigen

C03207ZK-4752016-delta Progesterone4,16-PREGNADIEN-3,20-DIONE17-Acetylandrosta-4,16-diene-3-one

delta(16)-ProgesteroneDTXCID801333848214-142-8.DELTA.16-Progesterone(8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-oneNSC 110374,16-Pregnadiene-3,20-dione16-?Dehydroprogesterone

Datenbank-Bezeichner

CAS: 1096-38-4
PubChem CID: 101964
DTXSID: DTXSID10862535
ChEBI: CHEBI:18204
UNII: JU0YQ9DZ2O
EC Number: 214-142-8
Nikkaji: J127.974B

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,9
Polarare Oberfläche (TPSA): 34,1 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 1
Schwere Atome: 23
Formalladung: 0
Komplexität: 640

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point185 - 187 °C

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt: 185 · 185-187 °C(lit.)
Siedepunkt: 461 · 461.0±45.0 °C(Predicted)
Dichte: 1.1 · 1.10±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
Löslichkeit: Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly)
Aggregatzustand: Solid
Farbe: Off-White to Pale Yellow
InChI: InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h6,12,16,18-19H,4-5,7-11H2,1-3H3/t16-,18-,19-,20-,21+/m0/s1
InChIKey: VRRHHTISESGZFN-RKFFNLMFSA-N
SMILES: C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(C(=O)C)=CC3)CC2
CAS Datenbank: 1096 · 1096-38-4(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (95.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, 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.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 25-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32360

Hazard Classes and CategoriesAcute Tox. 4 (95.1%)

Sicherheitsdaten

wgk: 3
risk_code: 20/21/22-40
hazard_code: Xn
safety_code: 22-36

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsExtracellular

Anwendungen · 1 Eintrag

Verwenden16-Dehydroprogesterone is used in the direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids. 16-Dehydroprogesterone is a form of Progesterone (P755900), a steroid hormone produced by the corpus luteum that induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.