(3aS,6Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Base Information

• Chemical Name: (3aS,6Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• CAS No.: 553-21-9
• Molecular Formula: C15H20O2
• Molecular Weight: 232.323
• Hs Code.: 29322090
• European Community (EC) Number: 683-148-4
• Wikipedia: Costunolide
• Mol file: 553-21-9.mol

Synonyms:costunolide;isocostunolide

Chemical Property of (3aS,6Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Chemical Property:

• Vapor Pressure: 3.8E-06mmHg at 25°C
• Melting Point: 106-109oC
• Refractive Index: 1.519
• Boiling Point: 385.4 °C at 760 mmHg
• Flash Point: 162 °C
• PSA: 26.30000
• Density: 1.03 g/cm³
• LogP: 3.55080
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: soluble10mg/mL (clear solution)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 232.146329876
• Heavy Atom Count: 17
• Complexity: 401

Purity/Quality:

95%-98% ^*data from raw suppliers

Costunolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CC2C(CC1)C(=C)C(=O)O2)C
• Isomeric SMILES: C/C/1=C/CCC(=C[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)C
• Description: Costunolide is a germacranolide sesquiterpene lactone extracted from costus oil. With alantolactone and dehydrocostuslactone, it is a component of lactone mix used to elicit reactions in Compositae-sensitive patients. An erythema-multiform-like occupational contact dermatitis case occurred in a chemistry student after accidental exposure to costus oil (CJ Le Coz & JP Lepoittevin, unpublished results).
• Uses: Costunolide is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases. (+)-Costunolide is an inhibitor of osteoclast differentiation, acting as an anti-inflammatory and anti-oxidant agent. It is a sesquiterpene lactone which mediates apoptosis.

Technology Process of (3aS,6Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

There total 30 articles about (3aS,6Z,11aR)-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

saussureamine A → costunolide (553-21-9)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(00)00696-7

Reference yield: 100.0%

(R)-2-Amino-3-((6E,10E)-(3S,3aS,11aS)-6,10-dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethylsulfanyl)-propionic acid → costunolide (553-21-9)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(00)00696-7

Reference yield: 100.0%

(S)-2-[((6E,10E)-(3R,3aS,11aS)-6,10-Dimethyl-2-oxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-3-ylmethyl)-amino]-5-guanidino-pentanoic acid → costunolide (553-21-9)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(00)00696-7

upstream raw materials:

1S,10R-3,7-dimethyl-10-<2-(1-hydroxy-2-propenyl)>-2E,6E-cyclodecadien-1-ol

(2E,6E)-8-((tert-butyldiphenylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-ol

Downstream raw materials:

6α-hydroxygermacra-1(10),4-diene

1,10-epoxycostunolide

Oxyreynosin

4-epiarbusculin A

Refernces

• 1、 Yang, Zhong-Jin,Ge, Wei-Zhi,Li, Qiu-Ying,Lu, Yaxin,Gong, Jian-Miao,Kuang, Bei-Jia,Xi, Xiaonan,Wu, Haiting,Zhang, Quan,Chen, Yue. "Syntheses and Biological Evaluation of Costunolide, Parthenolide, and Their Fluorinated Analogues". . p. 7007 - 7020. Retrieved 2015/09/22.