[(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methanol

• ChemBase ID: 165595
• Molecular Formular: C20H30O
• Molecular Mass: 286.4516
• Monoisotopic Mass: 286.22966558
• SMILES: C1C[C@]([C@H]2[C@](C1)(c1c(CC2)cc(cc1)C(C)C)C)(CO)C
• Canonical SMILES: OC[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(C)C)C
• InChI: InChI=1S/C20H30O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18,21H,5,7,9-11,13H2,1-4H3/t18-,19-,20+/m0/s1
• InChIKey: WSKGRAGZAQRSED-SLFFLAALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methanol
• IUPAC Traditional name: dehydroabietinol
• Synonyms: Dehydroabeityl Alcohol; Dehydroabietol; Dehydroabietyl alcohol; Pomiferin A; ar-Abietatrienol; [1R-(1α,4aβ,10aα)]-1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanol; Dehydroabietinol; (1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanol; 13-Isopropylpodocarpa-8,11,13-trien-15-ol; 8,11,13-Abietatrien-18-ol; Dehydroabietan-18-ol; Dehydroabietinol

Database IDs

• CAS Number: 3772-55-2
• PubChem SID: 162259728
• PubChem CID: 15586718

CALCULATED PROPERTIES

• Acid pKa: 15.108639
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 5.276301
• LogD (pH = 7.4): 5.276301
• Log P: 5.276301
• Molar Refractivity: 89.5015 cm^3
• Polarizability: 35.077194 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Oil

DETAILS

Toronto Research Chemicals - D229095

Dehydroabietinol is the hydroxy derivative of Dehydroabietic Acid (D229085) with antimicrobial activity. Dehydroabietinol also shows fungicidal activity againts wood contaminany fungi.

REFERENCES

• Gigante, B. et al.: Planta Med., 68, 680 (2002)
• Savluchinske-Feio, S. et al.: J. Microbiol. Meth., 70, 465 (2002)