Dihydrocostunolide

Base Information

• Chemical Name: Dihydrocostunolide
• CAS No.: 2225-79-8
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• Mol file: 2225-79-8.mol

Synonyms:Dihydrocostunolide;Germacra-1(10),4-dien-12-oic acid, 6.alpha.-hydroxy-, .gamma.-lactone, (E,E)-(11S)-;Cyclodeca(b)furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-3,6,10-trimethyl-, (3S-(3R*,3aR*,6E,10E,11aS*))-;Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-3,6,10-trimethyl-, [3S-(3R*,3aR*,6E,10E,11aR*)]-;2225-79-8;Cyclodeca[b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-3,6,10-trimethyl-, [3S-(3R*,3aR*,6E,10E,11aS*)]-;Costunolide, dihydro-;OVDMFKGCVWVONO-GYIATTAWSA-N;3,6,10-Trimethyl-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one #

Chemical Property of Dihydrocostunolide

Chemical Property:

• Vapor Pressure: 1.18E-05mmHg at 25°C
• Boiling Point: 369.5°Cat760mmHg
• Flash Point: 154.8°C
• Density: 0.969g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 365

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC(=CCCC(=CC2OC1=O)C)C
• Isomeric SMILES: CC1C2CC/C(=C\CC/C(=C\C2OC1=O)/C)/C
• General Description: (3S,3aS,10E,11aS)-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one, also known as dihydrocostunolide, is a germacranolide sesquiterpene lactone derived from costunolide. It exhibits biological activity as a germination stimulant for witchweed, showing efficacy across a broad concentration range (10^-5 to 10^-9 M), likely due to its germacrane skeleton and lactone ring structure. Additionally, its derivatives and synthetic analogs have demonstrated antifungal properties and potential as natural herbicide models, particularly in inhibiting radicle growth in monocotyledons. (3S,3aS,10E,11aS)-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2(3H)-one's structural features, including the spatial arrangement of the germacrane framework and the lactone moiety, are critical for its bioactivity, making it a promising lead for agrochemical and pharmaceutical applications.

Technology Process of Dihydrocostunolide

There total 15 articles about Dihydrocostunolide 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: 93.0%

costunolide (553-21-9) → 11βH,13-dihydrocostunolide (2225-79-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1016/S0040-4039(00)01334-4

Reference yield: 48.0%

Methanesulfonic acid (E)-(3S,3aS,10R,11R,11aS)-3,6,10-trimethyl-2-oxo-2,3,3a,4,5,8,9,10,11,11a-decahydro-cyclodeca[b]furan-11-yl ester (61228-90-8,70868-24-5,105882-30-2) → 11βH,13-dihydrocostunolide (2225-79-8)

Guidance literature:

With TBAO;

DOI:10.1021/jo00376a110

Reference yield:

C24H44O2Si (105882-28-8) → 11βH,13-dihydrocostunolide (2225-79-8)

Guidance literature:

Multi-step reaction with 9 steps

1: KF₂*2H₂O / hexamethylphosphoric acid triamide

3: MCPBA

4: OsO₄

5: PDC

6: NaBH₄

7: 92 percent

8: 66 percent / dimethyl diazomalonate, <(ν-C7H15CO2)2Rh>2

9: 48 percent / TBAO

With sodium tetrahydroborate; osmium(VIII) oxide; dipyridinium dichromate; KF*F^(1-); dimethyl diazomalonate; <(ν-C7H15CO2)2Rh>2; 3-chloro-benzenecarboperoxoic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00376a110

upstream raw materials:

costunolide

Methanesulfonic acid (E)-(3S,3aS,10R,11R,11aS)-3,6,10-trimethyl-2-oxo-2,3,3a,4,5,8,9,10,11,11a-decahydro-cyclodeca[b]furan-11-yl ester

(S)-2-((2E,7E)-(1R,4S)-4,8-Dimethyl-cyclodeca-2,7-dienyl)-propionic acid

(S)-2-((2E,7E)-(1R,4S)-4,8-Dimethyl-cyclodeca-2,7-dienyl)-propionic acid methyl ester

Downstream raw materials:

dihydro-β-cyclocostunolide

saussurea lactone

(3S,3aS,5aR,9aR,9bS)-3,5a,9-Trimethyl-3a,4,5,5a,6,7,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-one

11β,13-dihydroreynosin