6831-14-7

Basic information

• Product Name: (4aS,3aR)-5,6,6aα,7,9aβ,9bα-Hexahydro-1,4a,7α-trimethyl-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one
• Synonyms: (4aS,3aR)-5,6,6aα,7,9aβ,9bα-Hexahydro-1,4a,7α-trimethyl-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one;Arborescin
• CAS NO: 6831-14-7
• Molecular Formula: C15H20O3
• Molecular Weight: 248.3175
• Mol File: 6831-14-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 140-142°
• Boiling Point: 392.2°Cat760mmHg
• Flash Point: 165.4°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 2.33E-06mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: (4aS,3aR)-5,6,6aα,7,9aβ,9bα-Hexahydro-1,4a,7α-trimethyl-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,3aR)-5,6,6aα,7,9aβ,9bα-Hexahydro-1,4a,7α-trimethyl-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one(6831-14-7)
• EPA Substance Registry System: (4aS,3aR)-5,6,6aα,7,9aβ,9bα-Hexahydro-1,4a,7α-trimethyl-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one(6831-14-7)

Safety Data

• Hazardous Substances Data: 6831-14-7(Hazardous Substances Data)

Usage

Definition

ChEBI: An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is arglabin in which the exocyclic double bond has been reduced to a single bond. It is found in Artemesia adamsii.

InChI:InChI=1/C15H20O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,9-12H,5-7H2,1-3H3/t9-,10?,11+,12-,14-,15?/m0/s1

Upstream product

• 137624-14-7 1β,10β-Epoxyguaia-3,11(13)-dien-12,6α-olide 
• 149792-40-5 (11S)-1β-(mesyloxy)eudesm-3-eno-12,6α-lactone 
• 67895-36-7 (11S)-1β,10β-epoxy-3α-hydroxy-4βH-guaiano-13,6α-lactone 
• 82691-64-3 (11S)-1β,10β-epoxy-3α-(mesyloxy)-4βH-guaiano-13,6α-lactone 
• 67895-35-6 (11S)-3α-(benzoyloxy)-1β,10β-epoxy-4βH-guaiano-13,6α-lactone 

Relevant articles and documents

Synthesis and biological evaluation of antitumor-active arglabin derivatives

Arglabin derivatives varied at the endo- or exo-cyclic double bond were synthesized and studied in a colorimetric sulforhodamine B assay for their cytotoxicity. Variations on the endocyclic double bond led to compounds of reduced cytotoxicity whereas derivatives from the reaction of the α-methylene-γ-butyrolactone moiety led to compounds of similar or only slightly reduced cytotoxicity but different, cell line-dependent selectivity. In addition, arglabin is an excellent starting material for the synthesis of the guaianolide arborescin.

Synthesis of arborescin, 1,10-epiarborescin, and (11S)-guaia-3,10(14)-dieno-13,6α-lactone, the key intermediate in Greene and Crabbe's estafiatin synthesis, and the stereochemical assignment of arborescin

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