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566-48-3

Basic Information
CAS No.: 566-48-3
Name: Androst-4-ene-3,17-dione,4-hydroxy-
Article Data: 15
Cas Database
Molecular Structure:
Molecular Structure of 566-48-3 (Androst-4-ene-3,17-dione,4-hydroxy-)
Formula: C19H26O3
Molecular Weight: 302.414
Synonyms: 4-HAD;4-Hydroxyandrost-4-ene-3,17-dione;4-Hydroxyandrostene-3,17-dione;4-Hydroxyandrostenedione;4-OHA;CRC 82/01;Lentaron;NSC 282175;
EINECS: 625-331-3
Density: 1.19 g/cm3
Melting Point: 199-202 °C
Boiling Point: 475.4 °C at 760 mmHg
Flash Point: 255.4 °C
Solubility: N/A
Appearance: Needles
Hazard Symbols: ToxicT
Risk Codes: 60
Safety: 53-36/37/39-45
Transport Information: N/A
PSA: 54.37000
LogP: 3.97310
Synthetic route
77057-73-9

4,5-epoxyandrostane-3,17-dione

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
With sulfuric acid; silica gel; acetic acid at 70℃; for 0.05h;86%
With boron trifluoride diethyl etherate In benzene for 19h; Ambient temperature;47%
With formic acid for 0.75h; Heating;45%
Multi-step reaction with 2 steps
1: 62 percent / aq. sodium hydroxide / 3 h / Heating
2: 53 percent / hydrochloric acid / dioxane / 24 h / Heating
View Scheme
180303-17-7

3-hydroxy-5α-androst-2-ene-4,17-dione

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
With sodium In methanol for 1h; Ambient temperature;80%
With sodium In methanol at 20℃; for 1h;80%
With sodium methylate In methanol

3-hydroxy-5α-androst-2-ene-4,17-dione

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
With sodium In methanol for 1h; Ambient temperature;80%
434939-05-6

3β,4α-dihydroxy-5β-androstan-17-one

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
Stage #1: 3β,4α-dihydroxy-5β-androstan-17-one With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride In dichloromethane at -60℃; for 3h;
Stage #2: With sodium In methanol at 20℃; for 3h;
80%
Stage #1: 3β,4α-dihydroxy-5β-androstan-17-one With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride at -60℃; for 3.25h; Swern oxidation;
Stage #2: With sodium methylate In methanol
Multi-step reaction with 2 steps
1: TFAA; Et3N; DMSO / CH2Cl2 / 3 h / -60 °C
2: 80 percent / Na / methanol / 1 h / 20 °C
View Scheme
434939-09-0

3-hydroxy-5β-androst-2-ene-4,17-dione

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
With sodium In methanol at 20℃; for 1h;80%
501433-34-7

5α/β-androst-3-en-17-one

A

63-05-8

Androstenedione

B

1229-12-5

androstane-3,17-dione

C

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
Multistep reaction;A n/a
B n/a
C 54%
20986-46-3

4-methoxy-4-androstene-3,17-dione

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 24h; Heating;53%
64-19-7

acetic acid

77057-73-9

4,5-epoxyandrostane-3,17-dione

A

2241-85-2

2α-acetoxyandrost-4-ene-3,17-dione

B

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

C

571-17-5

2alpha-Hydroxyandrost-4-ene-3,17-dione

D

88509-26-6

4-hydroxyandrost-4,9(11)-diene-3,17-dione

Conditions
ConditionsYield
With sulfuric acid a) RT, 4 h, b) 4 deg C, 12 h; Further byproducts given;A 23%
B 52%
C 0.58 g
D 0.7 g
64-19-7

acetic acid

77057-73-9

4,5-epoxyandrostane-3,17-dione

A

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

B

571-17-5

2alpha-Hydroxyandrost-4-ene-3,17-dione

C

88509-26-6

4-hydroxyandrost-4,9(11)-diene-3,17-dione

D

140223-19-4

4α-acetoxy-5α-hydroxyandrostane-3,17-dione

Conditions
ConditionsYield
With sulfuric acid a) RT, 4h,b) 4 deg C, 12 h; Further byproducts given;A 52%
B 0.58 g
C 0.7 g
D 3%
77057-73-9

4,5-epoxyandrostane-3,17-dione

A

2241-85-2

2α-acetoxyandrost-4-ene-3,17-dione

B

566-48-3

4-hydroxyandrost-4-ene-3,17-dione

C

571-17-5

2alpha-Hydroxyandrost-4-ene-3,17-dione

D

88509-26-6

4-hydroxyandrost-4,9(11)-diene-3,17-dione

Conditions
ConditionsYield
With sulfuric acid In acetic acid a) RT, 4 h, b) 4 deg C, 12 h; Further byproducts given;A 23%
B 52%
C 0.58 g
D 0.7 g
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Specification

The Formestane, with the CAS registry number 566-48-3, is also known as 4-Hydroxyandrostenedione. It belongs to the product categories of Pharmaceutical Raw Materials; Miscellaneous Biochemicals; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. This chemical's molecular formula is C19H26O3 and molecular weight is 302.40794. Its IUPAC name is called (8R,9S,10R,13S,14S)-4-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione. it can be used as antitumor drug and aromatase inhibitor.

Physical properties of Formestane: (1)ACD/LogP: 2.66; (2)ACD/LogD (pH 5.5): 2.66; (3)ACD/LogD (pH 7.4): 2.66; (4)ACD/BCF (pH 5.5): 61.97; (5)ACD/BCF (pH 7.4): 61.22; (6)ACD/KOC (pH 5.5): 667.45; (7)ACD/KOC (pH 7.4): 659.45; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.569; (12)Molar Refractivity: 83.02 cm3; (13)Molar Volume: 253.1 cm3; (14)Surface Tension: 48.2 dyne/cm; (15)Density: 1.19 g/cm3; (16)Flash Point: 255.4 °C; (17)Enthalpy of Vaporization: 85.18 kJ/mol; (18)Boiling Point: 475.4 °C at 760 mmHg; (19)Vapour Pressure: 4.91E-11 mmHg at 25°C.

Preparation: this chemical can be prepared by 5-epoxy-5α-hsiung (steroid) alkyl-3,17-dione and methanol. This reaction will need CH3COOH, dichloromethane and hexane / ethyl acetate. The yield is about 47%.

When you are using this chemical, please be cautious about it as the following:
This chemical that at low levels can cause damage to health. It also may impair fertility. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC12CCC(=O)C(=C1CCC3C2CCC4(C3CCC4=O)C)O
(2)Isomeric SMILES: C[C@]12CCC(=O)C(=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
(3)InChI: InChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1
(4)InChIKey: OSVMTWJCGUFAOD-KZQROQTASA-N