(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

• ChemBase ID: 165594
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C1C[C@@]([C@H]2[C@](C1)(c1c(CC2)cc(cc1)C(C)C)C)(C)C(=O)O
• Canonical SMILES: OC(=O)[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(C)C)C
• InChI: InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1
• InChIKey: NFWKVWVWBFBAOV-MISYRCLQSA-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-octahydrophenanthrene-1-carboxylic acid
• IUPAC Traditional name: (-)-dehydroabietic acid
• Synonyms: (1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic Acid; 13-Isopropylpodocarpa-8,11,13-trien-15-oic Acid; (+)-Dehydroabietic acid; Abieta-8,11,13-trien-18-oic acid; NSC 2952; [1R-(1α,4aβ,10aα)]-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-Phenanthrenecarboxylic Acid; Dehydroabietic Acid

Database IDs

• CAS Number: 1740-19-8
• PubChem SID: 162259727
• PubChem CID: 94391

CALCULATED PROPERTIES

• Acid pKa: 4.5457826
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.7499404
• LogD (pH = 7.4): 2.9771657
• Log P: 5.7487645
• Molar Refractivity: 89.444 cm^3
• Polarizability: 35.01113 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D229085

Dehydroabietic Acid is a resin acid found commonly in rosin. Dehydroabietic Acid is used in rosin-type nucleating agent for polypropylene (PP). Dehydroabietic Acid is used commonly in the synthesis of surfactants, antioxidants and chiral catalysts.

REFERENCES

• Stricker, J.: Plaste Kautsch., 16, 481 (1969)
• Cui, G. et al.: Jing. Yu Zhuan. Huax., 14, 6 (1969)
• Wang, H. et al.: J. Appl. Polym. Sci., 89, 2137 (1969)