(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid

• ChemBase ID: 107695
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: CC(C)C1=CC2=CC[C@@H]3[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1
• Canonical SMILES: CC(C1=CC2=CC[C@@H]3[C@]([C@H]2CC1)(C)CCC[C@@]3(C)C(=O)O)C
• InChI: InChI=1S/C20H30O2/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/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
• InChIKey: RSWGJHLUYNHPMX-ONCXSQPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid
• IUPAC Traditional name: abietic acid
• Synonyms: (1R,4aR,4bR,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid; Abietinic acid; Sylvic acid; Abietic acid; (1R,4aR,4bR,10aR)-1,2,3,4,4a,4b,5,6,10,10a-Decahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic Acid; 13-Isopropylpodocarpa-7,13-dien-15-oic Acid; (-)-Abietic Acid; 7,13-Abietadien-18-oic Acid; Abietic Acid; NSC 25149; Odomit B 10; ZAO; l-Abietic Acid; Abietic Acid, 75%; Abietic acid; ABIETIC ACID PRACTICAL GRADE; 松香酸

Database IDs

• CAS Number: 514-10-3
• EC Number: 208-178-3; 208-173-3
• MDL Number: MFCD03423567
• Beilstein Number: 2221451
• PubChem SID: 24891449; 24844957; 162093761
• PubChem CID: 10569
• CHEBI ID: 28987
• CHEMBL: 71893
• Chemspider ID: 10127
• KEGG ID: C06087
• Unique Ingredient Identifier: V3DHX33184
• Wikipedia Title: Abietic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.589813
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.9930508
• LogD (pH = 7.4): 2.2175677
• Log P: 4.952565
• Molar Refractivity: 91.2142 cm^3
• Polarizability: 35.413227 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Very soluble in acetone, petroleum ether, Et₂O, and ethanol.
• Apperance: Powder; yellow resinous powder, crystals or chunks. Monoclinic plates (from EtOH/water).
• Melting Point: ~155 °C; 139-142 °C(lit.); 139-142°C; 140°C
• Boiling Point: 439.5°C
• Density: 1.06 g/mL
• Optical Rotation: [α]20/D -85±10°, c = 1% in ethanol

Safety Information

• RTECS: TP8580000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36/37/38-50/53; R36/37/38
• Safety Statements: 26-36; S26 S36
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• Main Hazard: Irritant, Not Good For Nature
• NFPA704:
  

  0

  1

  0
• GHS Hazard statements: H315-H319-H335-H400
• GHS Precautionary statements: P261-P273-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TNF(7124)

Product Information

• Purity: ~75% (GC); ≥65% (GC); 93.0
• Grade: PRACTICAL; technical
• Empirical Formula (Hill Notation): C20H30O2

DETAILS

MP Biomedicals - 05204616

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 00010

Other Notes
Starting material for natural product synthesis1,2,3; Epoxidation with MCPBA4

Toronto Research Chemicals - A108200

Abietic Acid is the primary component of resin acid found commonly in rosin. Abietic Acid exhibited potent testosterone 5α-reductase inhibitory activity in vitro.

REFERENCES

• Roh, S.-S. et al.: J. Health Sci., 56, 451 (2010)
• Harris, G.C. et al.: Org. Synth., 32, 1 (2010)