5956-15-0

Basic information

• Product Name: dihydroagathic acid
• Synonyms: dihydroagathic acid
• CAS NO: 5956-15-0
• Molecular Formula: C20H32 O4
• Molecular Weight: 336.47
• Mol File: 5956-15-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 486.7°C at 760 mmHg
• Flash Point: 262.2°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 8.33E-11mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: dihydroagathic acid(CAS DataBase Reference)
• NIST Chemistry Reference: dihydroagathic acid(5956-15-0)
• EPA Substance Registry System: dihydroagathic acid(5956-15-0)

Safety Data

• Hazardous Substances Data: 5956-15-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H32O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h13,15-16H,2,5-12H2,1,3-4H3,(H,21,22)(H,23,24)/t13?,15-,16+,19+,20+/m0/s1

Upstream product

• 640-28-8 labda-8⁽¹⁷⁾,13-diene-15,19-dioic acid 
• 159812-25-6 (E)-15-oxolabda-8⁽¹⁷⁾,13-diene-19-oic acid 
• 69308-72-1 isocupressic acid 
• 640-28-8 agathic acid 

Downstream Products

• 1757-83-1 dimethyl pinifolate 

Relevant articles and documents

Preparation of tetrahydroagathic acid: a serum metabolite of isocupressic acid, a cattle abortifacient in ponderosa pine.

Isocupressic acid (1) was used to synthetically prepare a mixture of (8S,13R,S)-labda-15,19-dioic acid (tetrahydroagathic acid) (5) via a two-step oxidation procedure followed by hydrogenation of the double bonds at C13 and C8. Reduction of the C8,17 double bond was stereospecific producing only the 8S isomer and confirmed by the nOe interaction between the resulting C17 and C20 methyl groups. The 13R and 13S isomers of 5 were separated and analyzed by HPLC/MS, and (13S)-tetrahydroagathic acid was isolated and identified by comparison to a standard prepared by hydrogenation of naturally occurring (13S)-dihydroagathic acid (4). (13R,S)-dihydroagathic acid was prepared by selective sodium metal-catalyzed hydrogenation of the C13,14 allylic double bond of agathic acid (3). The prepared compounds were then used as standards to confirm the presence of 4 and 5 and their respective 13R and 13S isomers in bovine serum samples. Tetrahydroagathic acid was shown to be the only metabolite detected in serum samples taken from a suspected cattle abortion case submitted for diagnosis; and, thus, 5 could be a valuable diagnostic marker for pine needle-induced abortions.

In vitro biotransformations of isocupressic acid by cow rumen preparations: Formation of agathic and dihydroagathic acids

Isocupressic acid [15-hydroxylabda-8(17),13E-dien-19-oic acid] (1) was incubated under anaerobic conditions for 48 h in an in vitro ruminal fluid mixture and was transformed into two metabolites. The two metabolites were identified by GC/MS as agathic acid [labda-8(17),13(E)-diene-15,19-dioic acid] (4E) and dihydroagathic acid [labda-8(17)-ene-15,19-dioic acid] (6). Metabolite identities were confirmed by chemical conversions of isocupressic acid (1) and imbricataloic acid (5) into 4E and 6, respectively. Structures of synthetic metabolites were confirmed by 1H and 13C NMR, specific rotation, GC/MS, and high-resolution mass spectrometry. Plasma obtained from cows that were fed Ponderosa pine needles contained (13R,S)-dihydroagathic acid (6) but not isocupressic acid (1) or 4E. The results suggest that isocupressic acid (1) is metabolically oxidized to agathic acid (4E), subsequently reduced to (13R,S)-dihydroagathic acid (6) in the rumen, and then absorbed into the bloodstream of cattle.