Epiandrosterone

Iupac Name：(3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one

CAS No.: 481-29-8

Molecular Weight：290.447

Modify Date.: 2022-11-29 12:15

Introduction:

A metabolite of testosterone or androstenedione with a 3-alpha-hydroxyl group and without the double bond.

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1. Names and Identifiers

1.1 Name: Epiandrosterone
1.2 Synonyms: (3S,5S,8R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one (3β,5α)-3-Hydroxyandrostan-17-one 3beta-Androsterone 3-Epiandrosterone 3-Hydroxyandrostan-17-one 3β-Androsterone 3β-Hydroxy-17-oxo-5α-androstane 3β-Hydroxy-5α-androstan-17-one 3β-Hydroxy-5α-androstane-17-one 3β-Hydroxyandrostan-17-one 3β-Hydroxyetioallocholan-17-one 3β-OH-5α-Androstane-17-one 5alpha-Androstan-17-one, 3beta-hydroxy- 5-Epiandrosterone-17-one 5α-Androstan-17-one, 3β-hydroxy- 5α-Androstan-17-one-3β-ol 5α-Androstan-3β-ol-17-one 5α-Androstane-3β-ol-17-one Androstan-17-one, 3-hydroxy-, (3beta,5alpha)- Androstan-17-one, 3-hydroxy-, (3β,5α)- Androsterone, epi- Androsterone, trans- d-Epiandrosterone epi-Androsterone Isoandrosterone iso-Androsterone NSC 93996 TRANS-ANDROSTERONE

1.3 CAS No.: 481-29-8

1.4 CID: 441302

1.5 EINECS(EC#): 207-563-3

1.6 Molecular Formula: C19H30O2 (isomer)

1.7 Inchi: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1

1.8 InChIkey: QGXBDMJGAMFCBF-LUJOEAJASA-N

1.9 Canonical Smiles: CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O

1.10 Isomers Smiles: C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O

2. Properties

2.1 Density: 1.085

2.1 Melting point: 171-177℃

2.1 Boiling point: 413.1 °C at 760 mmHg

2.1 Refractive index: 1.536

2.1 Flash Point: 176.4 °C

2.1 Precise Quality: 290.22500

2.1 PSA: 37.30000

2.1 logP: 3.95910

2.1 Appearance: white to off-white crystalline powder

2.2 Chemical Properties: white to off-white crystalline powder

2.3 Color/Form: Powder

2.4 pKa: 15.14±0.60(Predicted)

2.5 Water Solubility: Practically insoluble in water

2.6 Stability: Stable under normal temperatures and pressures.

2.7 StorageTemp: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Hormones and antibiotics room.

3. Use and Manufacturing

3.1 Definition: ChEBI: A 3beta-hydroxy steroid that is (5alpha)-androstane substituted by a beta-hydroxy group at position 3 and an oxo group at position 17.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 28 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (39.29%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (39.29%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (39.29%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H351 (39.29%): Suspected of causing cancer [Warning Carcinogenicity]
H361 (96.43%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, and P501

3.3 Methods of Manufacturing: Catalytic hydrogenation with 5-androstene-3β-ol-17-one 3-acetate on palladium carbon to obtain androstane-3β-ol-17one 3-acetate, which is then hydrolyzed with sodium hydroxide solution The product.

3.4 Purification Methods: Purify epi-androsterone via the acetate, hydrolyse this and recrystallise it from CHCl3/hexane or aqueous EtOH. The acetate [1239-31-2] is purified by chromatography and when crystallised from pet ether has m 103-104o, []D +68.5o (c 1, CHCl3). The oxime has m 194-196o (from MeOH), []D +17.5o (c 6.2, CHCl3). The racemic ketone is sublimed at 130o/high vacuum and after two crystallisations from methylcyclohexane it gives prisms with m 161-162o (which changed crystal form at 140-145o). [Ruzicka & Wettstein Helv Chim Acta 18 1264 1935, Johnson et al. J Am Chem Soc 75 2275 1953, 78 6331 1956, Cordwell et al. J Chem. Soc 361 1953, Beilstein 8 IV 462.] Epiandrosterone Preparation Products And Raw materials Raw materials

3.5 Usage: A metabolite of testosterone or androstenedione with a 3-alpha-hydroxyl group and without the double bond.

4. Safety and Handling

4.1 Safety Statements: S24/25

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P405, P501

4.1 WGK Germany: 3

4.1 Safety: Safety Statements:22-24/25
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
WGK Germany:3

4.2 Specification

The IUPAC name of?Epiandrosterone is?(3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one. With the?CAS registry number 481-29-8, it is also named as?3beta-Hydroxyetioallocholan-17-one. The?product's categories are?pharmaceutical intermediates; steroids; 17-ketosteroids; biochemistry; hydroxyketosteroids.?It?is?white to off-white crystalline powder whih?is used for steroid hormone drug.?It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. Additionally, Epiandrosterone should be sealed in the container?that the container is placed in the cool and dry aera.?Furthermore, people ahould?not breathe dust and avoid contact with skin and eyes.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 3.75; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 1; (6)Index of Refraction: 1.536; (7)Molar Refractivity: 83.49 cm³; (8)Molar Volume: 267.6 cm³; (9)Polarizability: 33.1×10^-24cm³; (10)Surface Tension: 41.1 dyne/cm; (11)Enthalpy of Vaporization: 76.93 kJ/mol; (12)Vapour Pressure: 1.5E-08 mmHg at 25°C; (13)Tautomer Count: 2; (14)Exact Mass: 290.22458; (15)MonoIsotopic Mass: 290.22458; (16)Topological Polar Surface Area: 37.3; (17)Heavy Atom Count: 21; (18)Complexity: 459.

Preparation of?Epiandrosterone: It?can?be converted from the natural steroids androstanediol via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase. And it?is also naturally?obtained by the enzyme 5-alpha reductase from the adrenal hormone dehydroepiandrosterone (DHEA).

People can use the following data to convert to the molecule structure.
1.SMILES:O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@@H](O)CC[C@]34C)C
2. InChI:InChI=1/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1B

Reproductive toxicity, Additional category for effects on or via lactation

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H360 May damage fertility or the unborn child H362 May cause harm to breast-fed children
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P263 Avoid contact during pregnancy and while nursing. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

7. Synthesis Route

481-29-8Total: 73 Synthesis Route

53-43-0 480 Suppliers

481-29-8 281 Suppliers

Literatures:
SAGE THERAPEUTICS, INC.; UPASANI, Ravindra, B.; HARRISON, Boyd, L.; ASKEW, Benny, C. Jr.; DODART, Jean-Cosme; SALITURO, Francesco, G.; ROBICHAUD, Albert, J. Patent: WO2013/36835 A1, 2013 ; Location in patent: Paragraph 00356 ;
Yield: ~97%

58-22-0

481-29-8 281 Suppliers

Literatures:
Dorfman; Fish Journal of Biological Chemistry, 1940 , vol. 135, p. 349
Yield: null

63-05-8 202 Suppliers

481-29-8 281 Suppliers

Literatures:
Wang, Chunli; Chen, Xiaoyu; Huang, Yaoqing; Yang, Jesse; Chen, Ying Steroids, 2013 , vol. 78, # 14 p. 1339 - 1346
Yield: null

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8. Precursor and Product

precursor:

516-55-2

53-43-0

897-06-3

53-41-8

853-23-6

63-05-8

571-20-0

521-18-6

846-46-8

product :

55569-05-6

521-11-9

51773-60-5

2429-15-4

1247-67-2

312-99-2

32326-39-9

53-41-8

25848-75-3

17752-36-2

57711-44-1

18339-16-7

59981-94-1

846-46-8

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9. Other Information

9.0 Storage Conditions: Catalytic hydrogenation with 5-androstene-3β-ol-17-one 3-acetate on palladium carbon to obtain androstane-3β-ol-17one 3-acetate, which is then hydrolyzed with sodium hydroxide solution The product.

9.1 Mesh Entry Terms: 3 alpha Hydroxy 5 alpha Androstan 17 One

9.2 Use Classification: Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]|Pharmaceuticals

10. Computational chemical data

Molecular Weight: 290.447g/mol
Molecular Formula: C₁₉H₃₀O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 290.224580195
Monoisotopic Mass: 290.224580195
Complexity: 459
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.3
Heavy Atom Count: 21
Defined Atom Stereocenter Count: 7
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYMAAAAAAAGDAAAAAGgAACAAADxSggAICAAAAAgAIAIAQAAAAAAAAAAAAAAEAAAAAEBIAAAAAQAAEAAAAAAGIyPCPgAAAAAAAAADAAAYAACAAAAAACAAAAA==

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