74841-81-9

Usage

Uses

Used in Pharmaceutical Industry:
(+)-CYCLOISOLONGIFOL-5-OL is used as a potential anti-inflammatory agent for its ability to reduce the production of inflammatory mediators. Its capacity to inhibit the growth of cancer cells positions it as a potential anticancer agent, offering a natural alternative for cancer treatment.
Additionally, (+)-CYCLOISOLONGIFOL-5-OL has shown inhibitory activity against certain enzymes, which suggests its potential use in the development of drugs targeting enzyme-related diseases or conditions. Ongoing research into its chemical structure and biological activities is expected to further elucidate its applications in medicine and healthcare.

InChI:InChI=1/C15H24O/c1-12(2)6-5-11(16)15-10-7-9(13(15,3)4)8-14(10,12)15/h9-11,16H,5-8H2,1-4H3/t9?,10?,11-,14+,15-/m1/s1

Upstream product

• 26619-54-5 isolongifolene epoxide 
• 59056-66-5 C₁₆H₂₄O 
• 59056-64-3 C₁₆H₂₆O 
• 103739-20-4 8,16-epoxy-8-methylisolongifolane 
• 103739-18-0 8-methyleneisolongifolane 
• 103739-23-7 C₁₆H₂₄O₂ 

Downstream Products

• 74842-33-4 dehydrocycloisolongifolene 
• 29476-92-4 (2R,4aS)-1,1,5,5-Tetramethyl-1,3,4,5,6,7-hexahydro-2H-2,4a-methano-naphthalen-4-ol 
• 74799-19-2 C₁₇H₂₆O₂ 
• 74813-20-0 Acetic acid (2R,4aS)-1,1,5,5-tetramethyl-1,3,4,5,6,7-hexahydro-2H-2,4a-methano-naphthalen-4-yl ester 

Relevant academic research and scientific papers

A Conveniant Preparation of Dehydrocycloisolongifolene and Its Conversion into 5-Oxoisolongifolene

Heating isolongifolene epoxide (4) with aluminium isopropoxide at 140 deg C / 1 h followed by distillation under reduced pressure gives a mixture which is converted entirely into 6 by exposure of the mixture as such to boron trifluoride-etherate in benzene.A 1,5-hydration of 6 gives the alcohol 9, oxidizable to 5-oxoisolongifolene (10) with Jones' reagent.

8-Methyleneisolongifolane/8-Methylisolongifolene: Synthesis and Reactions of Their Epoxides with Boron Trifluoride Etherate

Wittig olefination of 7αH-8-oxoisolongifolane (2) generates 7βH-8-methyleneisolongifolane (4), which on exposure to BF3*OEt2 smoothly rearranges to the tetrasubstituted 8-methylisolongifolene (5).Action of BF3*OEt2 on the two epoxides 6/7 derived from 4/5 results in the unusual formation of the primary alcohol (9)/olefin (10) involving a concomitant cyclopropanation in both the cases.The β-stereochemistry for the hydroxymethyl group at C-8 in 9 has been derived by a direct coorelation of 9 with the known C15-cyclopropyl secondary alcohol (17).The cyclopropyl olefin (10) has been synthesised by dehydration of the tertiary alcohol (24) (resulting from the methyllithium reaction of the ketone 23 derived from 17).Epoxidation-isomerization of 10 generates the tetracyclic ketone (25).