73069-14-4

Basic information

• Product Name: 2-ATRACTYLENOLIDE
• Synonyms: 2-ATRACTYLENOLIDE;ASTEROLIDE;(4aS,8aR,9aS)-4a,5,6,7,8,8a,9,9a-Octahydro-3,8a-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one;Atractylenolide Ⅱ
• CAS NO: 73069-14-4
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 73069-14-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 150-152 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 383.745oC at 760 mmHg
• Flash Point: 161.253oC
• Appearance: /
• Density: 1.092g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: 2-ATRACTYLENOLIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ATRACTYLENOLIDE(73069-14-4)
• EPA Substance Registry System: 2-ATRACTYLENOLIDE(73069-14-4)

Safety Data

• Hazardous Substances Data: 73069-14-4(Hazardous Substances Data)

Usage

General Description

2-Atractylenolide is a naturally occurring chemical compound found in the Atractylodes macrocephala Koidz plant, which is commonly used in traditional Chinese medicine. It has been reported to possess a variety of pharmacological activities, such as anti-inflammatory, anticancer, and antibacterial properties. 2-Atractylenolide has also shown potential in the treatment of inflammatory diseases and has been studied for its potential in cancer therapy. Research has indicated that 2-Atractylenolide has the ability to inhibit the growth of cancer cells and induce apoptosis, making it a promising candidate for further exploration in the field of cancer treatment. Additionally, 2-Atractylenolide may have potential in the development of new drugs for the treatment of various medical conditions, highlighting its importance in the field of medicinal chemistry.

InChI:InChI=1/C15H20O2/c1-9-11-6-4-5-7-15(11,3)8-12-13(9)10(2)14(16)17-12/h11-12H,1,4-8H2,2-3H3/t11-,12+,15-/m1/s1

Upstream product

• 470-17-7 isoalantolactone 
• 452-68-6 1-fluoro-4-iodo-2-methylbenzene 
• 74064-03-2 (3aR,4aS,8aR,9aS)-3,8a-Dimethyl-5-methylene-3-phenylsulfanyl-decahydro-naphtho[2,3-b]furan-2-one 
• 3484-43-3 (+/-)-atractylon 
• 2844-80-6 1,2,3,4,5,8-hexahydro-1-oxo-6-methoxynaphthalene 
• 1201-61-2 1,2,3,4,5,8-hexahydro-1-hydroxy-6-methoxynaphthalene 
• 3241-65-4 (+/-)-8a-methyl-5-methylene-octahydro-naphthalen-2(1H)-one 
• 162657-45-6 6-methoxy-4a-methyl-1-(trimethylsilyloxy)-2,3,4,4a,5,8-hexahydronaphthalene 
• 600151-49-3 6-methoxy-4a-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-one 
• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 
• 74842-02-7 (±)-ethyl (1R,2S)-2-methyl-4-oxo-2-vinylcyclohexane-1-carboxylate 
• 74842-03-8 (±)-ethyl (7S,8R)-7-methyl-7-vinyl-1,4-dioxaspiro[4.5]decane-8-carboxylate 
• 18664-32-9 1,3-dimethoxypropan-2-one 

Downstream Products

• 3484-43-3 (+/-)-atractylon 
• 182426-37-5 3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 
• 94204-13-4 9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one 
• 182426-37-5 (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 
• 182426-37-5 (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 
• 182426-37-5 3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 
• 6466-81-5 3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a-hexahydro-4H-naphtho[2,3-b]furan-2-one 
• 182426-37-5 (+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione 

Relevant articles and documents

Synthesis of a new class of bisheterocycles via the Heck reaction of eudesmane type methylene lactones with 8-bromoxanthines

The eudesmane-type methylene lactones (isoalantolactone, alantolactone, 4,15-epoxyisoalantolactone, 2′,2′-dichloro-4H-spiro[cyclopropane-1′,4-eudesma-11(13)-en-8β,12-olide], and alantolactone) react with 8-bromoxanthines (8-bromocaffeine, 8-bromotheobromine, 8-bromo-3-butyltheobromine, 8-bromotheophylline, 8-bromo-9-butyltheophylline) under Heck reaction conditions to produce the target (E)-13-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)eudesma-4(15),11(13)-dien-8β,12-olides and the subsequent endocyclic isomers - 11-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)-13-normethyleudecma-4(15)-7(11)-dien-8α,12-olides. It was revealed that the yield and product ratio depends on the reaction conditions and the structure of methylene lactone. The effectiveness of Pd(OAc)2–caffeine catalytic system has been demonstrated in this reaction. The electric eel acetylcholinesterase inhibitory activity of the eudecmanolide-xanthine hybrids was evaluated. Among the new type bisheterocycles compound 27 with butyl and 2-oxodecahydronaphtho[2,3-b]furan-3(2H)-ylidene)methyl substituents at C-7 and C-8 of the xanthine core showed moderate activity with IC50 value of 40?μM.

Synthetic transformations of methylenelactones of eudesmanic type. Behavior of isoalantolactone under the conitions of heck reaction

By Heck reaction of isoalantolactone with aryl bromides or aryl iodides (3aR,4aS, 8aR,9aR,E)-3-arylmethylidene-8a-methyl-5- methylidenedecahydronaphtho[2,3-b]furan-2(3H)-ones and (4aS,8aR,9aS)-3- arylmethyl-8a-methyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b] furan-2(4H)-ones, products of the double bond shift, were synthesized. The yields of the arylation products depend on the nature of the catalytic system and on the structure of the aryl halide. The structures of (3aR,4aS,8aR,9aR,E)- 3-(3,4-dimethoxybenzylidene)-8amethyl-5-methylidenedecahydronaphtho[2,3-b] furan-2(3H)-one and (4aS,8aR,9aS)-3-(2-methylsulfanylbenzyl)-8amethyl-5- methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one were proved by XRD analysis. Pleiades Publishing, Ltd., 2010.

Biomimetic synthesis of biatractylolide and biepiasterolide

(Matrix presented) The biomimetic synthesis of the bisesquiterpenoids biatractylolide 1 and biepiasterolide 2 is reported.