(3R,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

• ChemBase ID: 157518
• Molecular Formular: C30H48O3
• Molecular Mass: 456.70032
• Monoisotopic Mass: 456.3603454
• SMILES: C[C@@]12CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]3[C@@]4(CC[C@H]([C@]3(C)C(=O)O)O)C)C)[C@@H]1CC(CC2)(C)C)C
• Canonical SMILES: OC(=O)[C@@]1(C)[C@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C)C)C
• InChI: InChI=1S/C30H48O3/c1-25(2)14-15-26(3)16-17-28(5)19(20(26)18-25)8-9-21-27(4)12-11-23(31)30(7,24(32)33)22(27)10-13-29(21,28)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21+,22+,23+,26+,27+,28+,29+,30+/m0/s1
• InChIKey: BZXULBWGROURAF-IKNLXHIFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid
• IUPAC Traditional name: (3R,4R,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-hydroxy-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• Synonyms: 3α-Acetyl-α-boswellic Acid; alpha-Boswellic Acid; α-Boswellic Acid; (3α,4β)-3-Hydroxyolean-12-en-23-oic acid; 3α-Hydroxyolean-12-en-24-oic acid; α-Boswellic acid; 3-Hydroxyolean-12-en-24-oic acid; (3α,4β)-3-羟基齐墩果-12-烯-23-酸; 3α-羟基齐墩果-12-烯-24-酸; α-乳香酸

Database IDs

• CAS Number: 471-66-9
• MDL Number: MFCD03788779
• Beilstein Number: 3074442
• PubChem SID: 162251655
• PubChem CID: 637234

CALCULATED PROPERTIES

• Acid pKa: 4.5676003
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.6155386
• LogD (pH = 7.4): 3.841294
• Log P: 6.5948334
• Molar Refractivity: 133.6245 cm^3
• Polarizability: 53.23124 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C30H48O3

DETAILS

Toronto Research Chemicals - B676490

The principal constitutents of frankincense (olibanum). A specific, nonredox inhibitor of 5-lipoxygenase used to treat inflammation.

REFERENCES

• Safayhi, H. et al.: J. Pharmacol. Exp. Therap., 261, 1143 (1992)
• Siemoneit, U., et al.: Eur. J. Pharmacol., 606, 246 (1992)
• Cao, H. et al.: Pharamacol. Res., 61, 519 (1992)