4642-95-9

Basic information

• Product Name: trendione
• Synonyms: trendione;Estra-4,9,11-triene-3,17-dione;Estra-4,9,11-triene-3,17-dionea(Trenavar);Trenavar;Trendione Trenavar;(8S,13S,14S)-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS NO: 4642-95-9
• Molecular Formula: C₁₈H₂₀O₂
• Molecular Weight: 268.35
• Mol File: 4642-95-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 140℃
• Boiling Point: 489.403 °C at 760 mmHg
• Flash Point: 181.316 °C
• Appearance: /
• Density: 1.19
• Vapor Pressure: 1E-09mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: trendione(CAS DataBase Reference)
• NIST Chemistry Reference: trendione(4642-95-9)
• EPA Substance Registry System: trendione(4642-95-9)

Safety Data

• Hazardous Substances Data: 4642-95-9(Hazardous Substances Data)

Usage

Uses

trendione is a prohormone to trenbolone, a steroid growth promotor administered to beef cattle and reportedly abused by athletes. Estra-4,9,11-triene-3,17-dione is classified as a Schedule III controlled substance in the United States. This compound is intended for forensic and research purposes only.[Cayman Chemical]

InChI:InChI=1/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h8-10,15-16H,2-7H2,1H3/t15-,16+,18+/m1/s1

Synthetic route

Triethyl orthoacetate (78-39-7) + 11β-hydroxyestr-4,10-diene-3,17-dione → 3-hydroxy-estra-1,3,5(10),9(11)-tetraen-17-one (1089-80-1) + Trendione (4642-95-9) + ethyl 3,17-dioxoandrosta-4(5),9(11)-diene-19-carboxylate (135215-65-5)

Conditions	Yield
In propionic acid at 137℃; for 4h;	A 2% B 2% C 81%

trenbolone (10161-33-8) → Trendione (4642-95-9)

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;	76%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine Swern oxidation;

11β-hydroxyestr-4,10-diene-3,17-dione → 3-hydroxy-estra-1,3,5(10),9(11)-tetraen-17-one (1089-80-1) + Trendione (4642-95-9) + 11β-mercapto estra-4,9-diene-3,17-dione (160346-86-1)

Conditions	Yield
With perchloric acid; hydrogen sulfide In dichloromethane at 0℃; for 0.25h;

ethyl acetate n-hexane + ethylene glycol (107-21-1) + orthoformic acid triethyl ester (122-51-0) + Trendione (4642-95-9) → 3-ethylenedioxy-13β-methyl-gona-4,9,11-triene-17-one + 17α-chloromethyl-17β-hydroxy-13β-methyl-gona-4,9,11-triene-3-one

Conditions	Yield
With triethylamine; toluene-4-sulfonic acid In tetrahydrofuran; nitrogen; ethyl acetate	A n/a B 69%

Trendione (4642-95-9) + allylmagnesium bromide (1730-25-2) → Altrenogest (850-52-2)

Conditions	Yield
Stage #1: Trendione With hydrogenchloride In ethylene glycol at 10 - 60℃; for 10h; Autoclave; Stage #2: allylmagnesium bromide In tetrahydrofuran; diethyl ether at 0℃; for 6h; Temperature; Solvent; Autoclave;	65%

allylmagnesium bromide (2622-05-1) + Trendione (4642-95-9) → Altrenogest (850-52-2)

Conditions	Yield
Stage #1: Trendione With hydrogenchloride In ethylene glycol at 25 - 60℃; for 10h; Autoclave; Stage #2: allylmagnesium bromide In tetrahydrofuran; diethyl ether at 0℃; for 5h; Autoclave;	60%

Trendione (4642-95-9) → C20H26O5 (946848-69-7)

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water; tert-butyl alcohol	55%

ethylene glycol (107-21-1) + Trendione (4642-95-9) → C20H24O3 (15343-98-3)

Conditions	Yield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester

Upstream product

• 4642-77-8 AmoxycillinSodiumSterileBp983 
• 46427-20-7 4-bromo-3,5-dihydroxy-N-(2-hydroxyethyl)benzamide 
• 46426-73-7 3-guanidinobenzenesulfonic acid methyl ester 
• 4642-61-9 N-(5α-Androstan-3β-yl)acetamide 
• 4642-58-4 N-Acetyl-N-(5α-androst-2-en-3-yl)-L-alanine methyl ester 
• 46425-73-4 N-(2-Chlorobenzyl)cyclohexanamine 
• 46425-47-2 3-(2-CHLORO-2-PHENYLETHYL)-2-THIAZOLIDINIMINE 
• 4642-51-7 N-(5α-Androst-2-en-3-yl)-N-ethylacetamide 
• 4642-50-6 Spiro[5α-androstane-3,2'-thiazolidine] 
• 4642-37-9 5-(4-METHOXY-2-METHYLPHENYL)-5-OXOVALERIC ACID 
• 4642-35-7 5-(2-hydroxy-4-methylphenyl)-5-oxopentanoic acid 
• 4642-30-2 5-(4-METHOXY-3-METHYLPHENYL)-5-OXOVALERIC ACID 
• 464223-88-9 2-(1,3-benzothiazol-2-ylsulfanyl)-N'-(3-chlorobenzylidene)butanohydrazide 
• 464223-84-5 2-Butenoicacid,4-(2-ethyl-1-piperidinyl)-4-oxo-(9CI) 

Downstream Products

• 46429-76-9 N,N-DIMETHYL-3,5-DINITROANILINE 
• 4643-05-4 (E)-3-chloroprop-2-en-1-ol 
• 4643-06-5 (2E)-3-chloroprop-2-en-1-ol 
• 4643-19-0 N-(2-methoxyphenyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 4643-25-8 2 HEPTEN 4 ONE 
• 4643-27-0 2-OCTEN-4-ONE 
• 4643-36-1 N-METHYL-1-NAPHTHYLAMINE HYDROCHLORIDE 
• 464-34-6 2,4,6-tris[(2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptyl)oxy]-1,3,5-triazine 
• 4643-58-7 verrucarin J 
• 464-36-8 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-5-[(undecafluoropentyl)oxy]pentane 
• 4643-78-1 1-benzo[pqr]tetraphen-1-ylpropan-2-one 
• 46438-07-7 ETHYL 2-METHYLPHENYLALANINE 
• 46438-39-5 Phosphoric acid, monobutyl monophenyl ester 
• 4643-88-3 3-(4-methoxyphenyl)-1,2-oxazole-5-carboxamide 

Recommend Products

• 850-52-2  Altrenogest 
• 2622-05-1  allylmagnesium bromide 
• 1730-25-2  allylmagnesium bromide 
• 10161-33-8  trenbolone 
• 10161-33-8  trenbolone 
• 1089-80-1  3-hydroxy-estra-1,3,5⁽¹⁰⁾,9⁽¹¹⁾-tetraen-17-one 
• 160346-86-1  11β-mercapto estra-4,9-diene-3,17-dione 
• 135215-65-5  ethyl 3,17-dioxoandrosta-4⁽⁵⁾,9⁽¹¹⁾-diene-19-carboxylate 
• 78-39-7  Triethyl orthoacetate