67779-53-7

Basic information

• Product Name: 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran
• Synonyms: 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran;Pumiloxide
• CAS NO: 67779-53-7
• Molecular Formula: C20H30O
• Molecular Weight: 286.4516
• Mol File: 67779-53-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran(67779-53-7)
• EPA Substance Registry System: 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran(67779-53-7)

Safety Data

• Hazardous Substances Data: 67779-53-7(Hazardous Substances Data)

Upstream product

• 10395-42-3 trans-biformene 
• 17990-20-4 (12Z)-labda-8⁽¹⁷⁾,12,14-triene 
• 76467-13-5 (12R)-12,15-epidioxylabda-8⁽¹⁷⁾,13-diene 
• 76467-14-6 (12S)-12,15-epidioxylabda-8⁽¹⁷⁾,13-diene 
• 130451-52-4 ethyl 12,15-epoxylabda-8⁽¹⁷⁾,12,14-trien-16-oate 
• 130451-53-5 12,15-epoxylabda-8⁽¹⁷⁾,12,14-trien-16-ol 
• 106672-01-9 (1R,2R,8aS)-2,5,5,8a-tetramethyl-1-(2-oxoethyl)decahydronaphthalen-2-yl acetate 
• 52154-07-1 8α,13β-epoxy-15-norlabdan-14-oic acid 
• 5153-92-4 sclareol oxide 
• 130468-25-6 16-chloro-12,15-epoxylabda-8⁽¹⁷⁾,12,14-triene 

Relevant articles and documents

Labdanes, Withanolides, and Other Constituents from Physalis nicandroides

Chemical investigation of the aerial parts (except fruits and calixes) of Physalis nicandroides var. attenuata led to the isolation of a series of new labdane-type diterpenoids, including the closely related compounds 1-3, the labdane glucosides 4 and 5, a mixture of the epimeric alcohols 6 and 7, and one labdanetriol, isolated as its tri-O-acetyl derivative 9. In addition, three new withanolides (14-16) and six known compounds were isolated. The structures of these compounds were elucidated by analysis of their spectroscopic data and chemical transformations, and those of compounds 1, 4, and 16 were confirmed by X-ray diffraction analysis of the natural product (1) and of the corresponding acetyl derivatives 4a and 16a. Fourteen of these compounds were assayed for their in vitro inhibitory activity against yeast α-glucosidase and acetylcholinesterase enzymes. The results were negative in both cases, except for compound 3a that marginally inhibited the activity of acetylcholinesterase with an IC50 value of 64.4 μM.

Photosensitized Oxygenation of Labda-8(17),12-diene, Labda-8(17),13-diene, and the Biformenes. Synthesis of Pumiloxide

Reactions of the title compounds with singlet oxygen were studied.In labda-8(17),12-diene (2; 7:3 mixture of E and Z isomers), syn addition leading to 7 (58percent) was predominant.Smaller amounts of 8 (20percent) by syn addition to (E)-2 or anti addition to (Z)-2, 9 (5percent), 10 (2,5percent), and 11(1.5percent) were also formed. (E)-Labda-8(17),13-diene ((E)-3) gave 29percent 12 and 40percent 13 by syn addition, whereas (Z)-3 gave 57percent 12 by syn addition and 19percent 13 by anti addition.In trans-biformene (5) syn attack at C-12 to give 15 (27percent), 16 (10percent), 18 (12percent), and 19 (4percent) was greatly preferred to syn attack at C-13 to give 17 (6percent).In cis-biformene (6) syn attack at C-13 to give 17 (39percent) predominated slightly over anti attack at C-12 to give 15 (13percent), 16 (8percent), 18 (4percent), and 19 (4percent).Diels-Alder reactions with singlet oxygen leading to epidioxides 20 and 21 were relatively unimportant (7percent from 5, 5percent from 6).The epidioxides were converted to the naturally occurring furanolabdane pumiloxide (22).