(3S,7S)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one

• ChemBase ID: 155318
• Molecular Formular: C18H26O5
• Molecular Mass: 322.39604
• Monoisotopic Mass: 322.17802393
• SMILES: C[C@H]1CCC[C@H](CCCCCc2cc(cc(c2C(=O)O1)O)O)O
• Canonical SMILES: O[C@H]1CCCCCc2cc(O)cc(c2C(=O)O[C@H](CCC1)C)O
• InChI: InChI=1S/C18H26O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,14,19-21H,2-9H2,1H3/t12-,14-/m0/s1
• InChIKey: DWTTZBARDOXEAM-JSGCOSHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7S)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
• IUPAC Traditional name: β-zearalanol
• Synonyms: (3S,7S)-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one; P 1560; Taleranol; β-Zearalanol; β-Zearanol; β-Zeranol; 2,4-Dihydroxy-6-(6β,10-dihydroxyundecyl]benzoic acid μ-lactone; β-Zearalanol

Database IDs

• CAS Number: 42422-68-4
• MDL Number: MFCD00151077
• PubChem SID: 162249456; 24902165
• PubChem CID: 65434

CALCULATED PROPERTIES

• Acid pKa: 8.677322
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.4456
• LogD (pH = 7.4): 4.423684
• Log P: 4.4458866
• Molar Refractivity: 88.251 cm^3
• Polarizability: 34.207417 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 134-137°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-36/37/38
• Safety Statements: 53-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H360
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... Ar(24208)

Product Information

• Purity: ~98% (HPLC)
• Empirical Formula (Hill Notation): C18H26O5

DETAILS

Toronto Research Chemicals - Z346005

Animal growth promotant. Anabolic. Controlled substance.

REFERENCES

• Baldwin, R.S., et al.: Regul. Toxicol. Pharmacol., 3, 9 (1983)
• Lemieux, P.G., et al.: J. Anim. Sci., 68, 1702 (1983)