Dehydrocostus lactone

Base Information

• Chemical Name: Dehydrocostus lactone
• CAS No.: 477-43-0
• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.307
• Hs Code.: 29322090
• European Community (EC) Number: 683-106-5
• UNII: 71TRF5K040
• DSSTox Substance ID: DTXSID80891554
• Nikkaji Number: J12.433H
• Wikidata: Q27105152
• Metabolomics Workbench ID: 52740
• ChEMBL ID: CHEMBL88985
• Mol file: 477-43-0.mol

Synonyms:dehydrocostus lactone;dehydrocostuslactone

Chemical Property of Dehydrocostus lactone

Chemical Property:

• Vapor Pressure: 4.31E-06mmHg at 25°C
• Melting Point: 57.0 to 61.0 °C
• Refractive Index: 1.536
• Boiling Point: 383.7 °C at 760 mmHg
• Flash Point: 161.2 °C
• PSA: 26.30000
• Density: 1.09 g/cm³
• LogP: 3.01660
• Storage Temp.: room temp
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 230.130679813
• Heavy Atom Count: 17
• Complexity: 432

Purity/Quality:

Dehydrocostus Lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=C1CCC2C(C3C1CCC3=C)OC(=O)C2=C
• Isomeric SMILES: C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1CCC3=C)OC(=O)C2=C
• Description: A guaianolide sesquiterpene lactone extracted from costus oil. Dehydrocostuslactone is one of the components of lactone-mix, with costunolide and alantolactone, used to detect Compositae-sensitive patients. Dehydrocostus lactone is a natural sesquiterpene first isolated from costus root, which is used in traditional medicine. Dehydrocostus lactone has diverse anti-cancer properties in cells and animal models, causing cell cycle arrest, inducing apoptosis, diminishing multidrug resistance, and suppressing angiogenesis in cancer cells. It also has anti-inflammatory actions in cells, including the inhibition of signaling through STAT1 and STAT3.
• Uses: Dehydrocostus lactone is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases. Dehydrocostus Lactone is a compound known to be a growth regulator in plants. Known to affect cell viability and cell cycle distribution it may be useful in the application towards drug-resistant tumors.

Technology Process of Dehydrocostus lactone

There total 55 articles about Dehydrocostus lactone 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%

(3R,3aR,6aR,9aR,9bR)-3-Methyl-6,9-dimethylene-3-phenylselanyl-decahydro-azuleno[4,5-b]furan-2-one (90807-55-9) → dehydrocostus lactone (74299-48-2,93219-83-1,477-43-0)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; acetic acid;

DOI:10.1246/cl.1984.493

Reference yield: 100.0%

saussureamine B (126209-82-3) → dehydrocostus lactone (74299-48-2,93219-83-1,477-43-0)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 12h;

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

Reference yield: 100.0%

saussureamine C → dehydrocostus lactone (74299-48-2,93219-83-1,477-43-0)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 12h;

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

upstream raw materials:

(3R,3aR,6aR,9aR,9bR)-3-Methyl-6,9-dimethylene-3-phenylselanyl-decahydro-azuleno[4,5-b]furan-2-one

watsonol A

saussureamine B

[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-acetic acid

Downstream raw materials:

(3aS,9bS)-6,9-Dimethylene-3-(2-oxo-propyl)-decahydro-azuleno[4,5-b]furan-2-one

3α-hydroxyguaia-4(15),10(14),11(13)-trien-12,6-olide

zaluzanin C

3α,5α-dihydroxyguaia-4(15),10(14),11(13)-trien-12,6-olide

Refernces

• 1、 Kaden, Felix,Metz, Peter. "Enantioselective Total Synthesis of the Guaianolide (-)-Dehydrocostus Lactone by Enediyne Metathesis". . p. 1344 - 1348. Retrieved 2021/02/20.
• 2、 Matsuda, Hisashi,Kageura, Tadashi,Inoue, Yasunao,Morikawa, Toshio,Yoshikawa, Masayuki. "Absolute stereostructures and syntheses of saussureamines A, B, C, D and E, amino acid-sesquiterpene conjugates with gastroprotective effect, from the roots of Saussurea lappa". . p. 7763 - 7777. Retrieved 2007/10/03.