10180-86-6

Basic information

• Product Name: (3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate
• CAS NO: 10180-86-6
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.3377
• Mol File: 10180-86-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 466.6°C at 760 mmHg
• Flash Point: 207.1°C
• Density: 1.22g/cm³
• Vapor Pressure: 6.95E-09mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: (3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate(10180-86-6)
• EPA Substance Registry System: (3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate(10180-86-6)

Safety Data

• Hazardous Substances Data: 10180-86-6(Hazardous Substances Data)

Usage

Description

(3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate is a complex organic compound belonging to the diterpene class, characterized by its molecular formula C17H22O5. It is commonly found in the essential oils of certain aromatic herbs and is known for its diverse biological activities.

Uses

Used in Food Industry:
(3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate is used as a flavoring agent and preservative for its antimicrobial properties, contributing to the enhancement of food quality and shelf life.
Used in Pharmaceutical Industry:
(3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate is used as an active pharmaceutical ingredient for its anti-inflammatory, antioxidant, and antimicrobial properties, playing a role in the development of treatments for various health conditions.
Used in Medicinal Applications:
(3aR,4S,4aR,7aR,8R,9aR)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate is used as a potential therapeutic agent for the treatment of skin disorders, gastrointestinal issues, and respiratory conditions, due to its diverse biological activities and ongoing research into its mechanisms and therapeutic uses.

Upstream product

• 73407-89-3 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-4,5-bis<(tetrahydro-2H-pyran-2-yl)oxy>-azuleno<6.5-b>furan-2(3H)-one 
• 68241-56-5 (3aR,4R,4aS,5S,7aR,8R,9aS)-4a,8-Dimethyl-4,5-bis-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one 
• 71686-37-8 (3aα,4α,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one 
• 71686-37-8 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>-furan-2(3H)-one 
• 68241-57-6 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-4,5-dihydroxy-3-methylene-4a,8-dimethylazuleno<6,5-b>-furan-2(3H)-one 
• 73407-87-1 (3aR,4R,4aS,5S,7aR,8R,9aS)-5-Benzyloxy-4a,8-dimethyl-4-(tetrahydro-pyran-2-yloxy)-3a,4,4a,5,7a,8,9,9a-octahydro-3H-azuleno[6,5-b]furan-2-one 
• 73407-84-8 (3aS,4aR,5R,7aS,8S,9aR)-5-Benzyloxy-4a,8-dimethyl-3,3a,4a,5,7a,8,9,9a-octahydro-azuleno[6,5-b]furan-2,4-dione 
• 73407-88-2 (3aα,4β,4aβ,5β,7aα,8α,9aβ)-3a,4,4a,5,7a,8,9,9a-Octahydro-8-hydroxy-4a,8-dimethyl-4-<(tetrahydro-2H-pyran-2-yl)oxy>-azyleno<6,5-b>furan-2(3H)-one 
• 108-24-7 acetic anhydride 
• 5945-41-5 dl-Mexicanin I 
• 20483-26-5 2α,6α-diacetoxy-4β-hydroxy-pseudoguaia-11(13)-en-12,8α-olide 
• 6754-13-8 Helenalin 

Relevant articles and documents

Preparation of sesquiterpene lactone derivatives: Cytotoxic activity and selectivity of action

Cancer is one of the most important causes of death worldwide. Solid tumors represent the great majority of cancers (>90%) and the chemotherapeutic agents used for their treatment are still characterized by variable efficacy and toxicity. Sesquiterpene lactones are a group of naturally occurring compounds that have displayed a diverse range of biological activities including cytotoxic activity. A series of oxygenated and oxy-nitrogenated derivatives (4–15) from the sesquiterpene lactones cumanin (1), helenalin (2), and hymenin (3) were synthesized. The silylated derivatives of helenalin, compounds 13 and 14, were found to be the most active against tumor cell lines, with GI50 values ranging from 0.15 to 0.59 μM. The ditriazolyl cumanin derivative (11) proved to be more active and selective than cumanin in the tested breast, cervix, lung, and colon tumor cell lines. This compound was the least toxic against splenocytes (CC50 = 524.1 μM) and exhibited the greatest selectivity on tumor cell lines. This compound showed a GI50 of 2.3 μM and a SI of 227.9 on WiDr human colon tumor cell lines. Thus, compound 11 can be considered for further studies and is a candidate for the development of new antitumor agents.

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Chemical modification of Britanin and of inuchenolide C

Analogs of helenalin possessing a broad spectrum of biological activity have been synthesized from the readily available sesquiterpene lactones britanin and inuchenolide C. Conditions for the hydrolysis, oxidative transformations, and skeletal rearrangements of the pseudoguaianolides that are characteristic for plants of the genus Inula have been studied.

Antineoplastic agents. 34. Helenium autumnale L.

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