73069-13-3

Basic information

• Product Name: Atractylenolide-1
• Synonyms: ATRACTYLENOLIDE-1;(4aS,8aS)-4a,5,6,7,8,8a-Hexahydro-3,8a-dimethyl-5-methylenenaphtho[2,3-b]furan-2(4H)-one;3,8aβ-Dimethyl-5-methylene-2,4,4aα,5,6,7,8,8a-octahydronaphtho[2,3-b]furan-2-one;Eudesma-4(15),7(11),8-trien-12-olide;8,9-Dehydroasterolide;Atractylenolide Ⅰ;Naphtho[2,3-b]furan-2(4H)-one,4a,5,6,7,8,8a-hexahydro-3,8a-dimethyl-5-methylene-, (4aS,8aS)-
• CAS NO: 73069-13-3
• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.3
• Mol File: 73069-13-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 121-123 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 405 °C at 760 mmHg
• Flash Point: 170℃
• Appearance: /
• Density: 1.12
• Vapor Pressure: 9.08E-07mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble1mg/mL, clear, colorless
• CAS DataBase Reference: Atractylenolide-1(CAS DataBase Reference)
• NIST Chemistry Reference: Atractylenolide-1(73069-13-3)
• EPA Substance Registry System: Atractylenolide-1(73069-13-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 73069-13-3(Hazardous Substances Data)

Usage

Description

Atractylenolide-1 is a sesquiterpene compound found in the rhizomes of Atractylodes macrocephala, which exhibits a range of biological activities such as anti-inflammatory, anti-angiogenic, anti-tumor, and antidepressant properties. It has been shown to inhibit the production of TNF-α and nitric oxide (NO), as well as the activity of inducible nitric oxide synthase (iNOS) in murine peritoneal macrophages. Atractylenolide-1 also demonstrates the ability to reduce inflammation, granuloma weight, and vascular index in a mouse air pouch granuloma model induced by Freund's complete adjuvant (FCA). Additionally, it has been observed to inhibit the growth of various bladder cancer cell lines and exert antidepressant-like activity in a mouse model of depression.

Uses

Used in Pharmaceutical Industry:
Atractylenolide-1 is used as an anti-inflammatory agent for its ability to inhibit LPS-induced increases in TNF-α and NO production, as well as iNOS activity in murine peritoneal macrophages.
Atractylenolide-1 is used as an anti-angiogenic agent for its capacity to reduce the number of microvessels in the air pouch wall and decrease the blood levels of various growth factors in a mouse model of FCA-induced granuloma.
Atractylenolide-1 is used as an anti-tumor agent for its effectiveness in inhibiting the growth of T-24, 5637, RT4, and 253J bladder cancer cells in vitro and reducing tumor growth in T-24 and 253J mouse xenograft models in a dose-dependent manner.
Atractylenolide-1 is used as an antidepressant for its ability to reverse stress-induced decreases in hippocampal levels of serotonin and norepinephrine and reduce immobility time in the forced swim and tail suspension tests in a mouse model of depression induced by chronic unpredictable mild stress.

InChI:InChI=1/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3/t12-,15+/m0/s1

Upstream product

• 2844-80-6 1,2,3,4,5,8-hexahydro-1-oxo-6-methoxynaphthalene 
• 81053-87-4 (Z)-2-<(1aα,3aβ,7aα,7bβ)-3,3a,4,5,6,7,7a,7b-Octahydro-7a-methyl-4-methylennaphth<1,2-b>oxiren-2(1aH)-yliden>propionsaeure-methylester 
• 81053-81-8 (1'α,4'aβ,8'aα)-Decahydro-8'a-methyl-5'-oxospiro<1,3-dioxolan-2,3'-naphthalin>-1'-carbonsaeure-methylester 
• 81053-79-4 (1'α,4'aα,5'α,8'aα)-Decahydro-5'-hydroxy-8'a-methylspiro<1,3-dioxolan-2,3'-naphthalin>-1'-carbonsaeure-methylester 
• 81053-82-9 (1'α,4'aβ,8'aα)-Decahydro-8'a-methyl-5'-methylenspiro<1,3-dioxolan-2,3'-naphthalin>-1'-carbonsaeure-methylester 
• 81053-78-3 cis-1',2',3',4',6',7',8',8'a-Octahydro-8'a-methylspiro<1,3-dioxolan-2,3'-naphthalin>-1'-carbonsaeure-methylester 
• 51417-17-5 8a-methyl-3-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 81053-83-0 (1α,4aβ,8aα)-Decahydro-8a-methyl-5-methylen-3-oxo-1-naphthalincarbonsaeure 
• 81053-86-3 (1aα,3aβ,7aα,7bβ)-3,3a,4,5,6,7,7a,7b-Octahydro-7a-methyl-4-methylennaphth<1,2-b>oxiren-2(1aH)-on 
• 81053-85-2 trans-4a,5,6,7,8,8a-Hexahydro-4a-methyl-8-methylen-2(1H)-naphthalinon 
• 600151-49-3 6-methoxy-4a-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-one 
• 162657-45-6 6-methoxy-4a-methyl-1-(trimethylsilyloxy)-2,3,4,4a,5,8-hexahydronaphthalene 
• 3241-66-5 4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one 
• 3241-65-4 (+/-)-8a-methyl-5-methylene-octahydro-naphthalen-2(1H)-one 

Downstream Products

• 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 
• 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 

Relevant articles and documents

Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (±)-biatractylolide and (±)- biepiasterolide

The biomimetic synthesis of the bisesquiterpene lactones (±)-biatractylolide 1 and (±)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

Terpenes and Terpene Derivatives, XIII. - Synthesis of (+/-)-8,9-Dehydroasterolide

From the ketoester 2 the α,β-unsaturated ketone 9 is prepared via ketalization (--> 3), hydroboration (--> 4), oxidation (--> 6), Wittig reaction (--> 7), hydrolysis (--> 8a), and oxidative decarboxylation. 9 is a useful starting material for the synthesis of 8,9-dehydroasterolide (1) via epoxidation (--> 10), PO olefination (--> 11), hydrolysis (--> 12), and dehydratization.