Basic information
- CAS
1096-38-4- 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- Molecular formula
- C21H28O2
- Average molar mass
- 312.4 g/mol
- Monoisotopic mass
- 312.20893014
Overview
16,17-didehydroprogesterone is a 20-oxo steroid, a 3-oxo-Delta(4) steroid and an enone. It is functionally related to a progesterone.
Names & identifiers
- Preferred 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
- English name
- 16-Dehydroprogesterone
- Molecular formula
- C21H28O2
- Molecular weight
- 312.45
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
1096-38-4- PubChem CID
- 101964
- DTXSID
DTXSID10862535- ChEBI
CHEBI:18204- UNII
- JU0YQ9DZ2O
- EC Number
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 640
Experimental & physicochemical properties
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
Physicochemical properties
- Melting point
- 185 · 185-187 °C(lit.)
- Boiling point
- 461 · 461.0±45.0 °C(Predicted)
- Density
- 1.1 · 1.10±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly)
- form
- Solid
- color
- 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
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Regulatory InformationStatus: Active Update: 25-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32360
Hazard Classes and CategoriesAcute Tox. 4 (95.1%)
Safety data
- wgk
- 3
- risk_code
- 20/21/22-40
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 22-36
- Hazard statements
- H302-H312-H332-H351
- REACH Registrations
- Active
- Precautionary statements
- P280
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
Uses16-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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers68 total
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海腾准生物科技有限公司19821570922 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Related reactions
2 records
Compound notes
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