26931-94-2

Basic information

• Product Name: (3aR,4S,6E,10Z,11aR)-3a,4,5,8,9,11a-Hexahydro-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylenecyclodeca[b]furan-2(3H)-one
• Synonyms: (+)-Salonitenolide;(3aR,4S,6E,10Z,11aR)-3a,4,5,8,9,11a-Hexahydro-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylenecyclodeca[b]furan-2(3H)-one;(3aR,4S,6E,10Z,11aR)-3a,4,5,8,9,11a-Hexahydro-4-hydroxy-10-hydroxymethyl-6-methyl-3-methylenecyclodeca[b]furan-2(3H)-one;Salonitenolide
• CAS NO: 26931-94-2
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.3169
• Mol File: 26931-94-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 504.5°Cat760mmHg
• Flash Point: 190.3°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 2.72E-12mmHg at 25°C
• Refractive Index: 1.56
• PKA: 13.87±0.60(Predicted)
• CAS DataBase Reference: (3aR,4S,6E,10Z,11aR)-3a,4,5,8,9,11a-Hexahydro-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylenecyclodeca[b]furan-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,6E,10Z,11aR)-3a,4,5,8,9,11a-Hexahydro-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylenecyclodeca[b]furan-2(3H)-one(26931-94-2)
• EPA Substance Registry System: (3aR,4S,6E,10Z,11aR)-3a,4,5,8,9,11a-Hexahydro-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylenecyclodeca[b]furan-2(3H)-one(26931-94-2)

Safety Data

• Hazardous Substances Data: 26931-94-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3/b9-4+,11-7-/t12-,13+,14+/m0/s1

Upstream product

• 24394-09-0 cnicin 

Downstream Products

• 26931-87-3 (6R,7S,8S)-6,15-dihydroxygermacra-1⁽¹⁰⁾,4,11⁽¹³⁾-trien-8,12-olide 
• 22553-66-8 (+)-β-cyclopyrethrosin 

Relevant articles and documents

Sesquiterpene lactones from Centaurea arbutifolia

The investigation of the aerial parts of Centaurea arbutifolia afforded four new sesquiterpene lactones; two germacranolides and two elemanolides, plus aguerin A. Their structures were elucidated by spectroscopic methods and by partial synthesis.

Synthetic study of cnicin: Synthesis of the side chain and its esterification

Cnicin is a germacranolide sesquiterpene lactone that possesses potent inhibitory activity against the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT). Although cnicin has an interesting structure and attractive biological activity, synthetic studies of cnicin have not yet been reported. This report describes the synthesis of the protected side chain carboxylic acid moiety at C8 of cnicin via two routes starting from L-ascorbic acid. In addition, esterification between the synthetic side chain and salonitenolide derivative, which can be achieved via hydrolysis of cnicin and protection of the primary alcohol, was conducted. Thus, a semi-synthesis of cnicin was achieved.

Microbial transformation of sesquiterpene lactones by the fungi Cunninghamella echinulata and Rhizopus oryzae

Incubations of the fungi Cunninghamella echinulata and Rhizopus oryzae with the sesquiterpene lactones (+)-costunolide (1), (+)-cnicin (2), (+)- salonitenolide (3), (-)-dehydrocostuslactone (4), (-)-lychnopholide (5), and (-)-eremantholide C (6) were performed. Incubation of 1 with C. echinulata afforded Δ(11(13))-dihydrogenation and Δ(1(10))-epoxidation products (7- 10). C. echinulata also hydrolyzed the side chain of 2, and transformed 4 into (+)-11α,13-dihydrodehydrocostuslactone (12), a new natural product. R. oryzae converted 4 into both Δ(11(13))-dihydrogenation and Δ(10(14))- epoxidation products (16 and 17). Both fungi transformed 5 into (-)-16-(1- methyl-1-propenyl)eremantholanolide (13), providing experimental evidence for the biosynthesis of the eremantholide hemiketal unit. Compounds 3 and 6 were not metabolized by either fungus under the test conditions.