477-43-0

Basic information

• Product Name: Dehydrocostus lactone
• Synonyms: EPILIGULYL OXIDE;DEHYDROCOSTUSLACTONE;DEHYDROCOSTUS LACTONE hplc;(3aS,6aR,9aR,9bS)-Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one;DEHYDROCOSTUNOLIDE;Azuleno[4,5-b]furan-2(3H)-one,decahydro-3,6,9-;Costus lactone, dehydro-;tris(methylene)-,(3aS,6aR,9aR,9bS)-
• CAS NO: 477-43-0
• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.3
• Product Categories: Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Sesquiterpenoids
• Mol File: 477-43-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 57.0 to 61.0 °C
• Boiling Point: 383.7 °C at 760 mmHg
• Flash Point: 161.2 °C
• Appearance: /
• Density: 1.09
• Vapor Pressure: 4.31E-06mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: room temp
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Dehydrocostus lactone(CAS DataBase Reference)
• NIST Chemistry Reference: Dehydrocostus lactone(477-43-0)
• EPA Substance Registry System: Dehydrocostus lactone(477-43-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 477-43-0(Hazardous Substances Data)

Usage

Description

Dehydrocostus lactone is a natural sesquiterpene lactone, a guaianolide sesquiterpene lactone, and an organic heterotricyclic compound. It is extracted from costus oil and is one of the components of lactone-mix, along with costunolide and alantolactone. Dehydrocostus lactone is known for its diverse anti-cancer properties, causing cell cycle arrest, inducing apoptosis, diminishing multidrug resistance, and suppressing angiogenesis in cancer cells. It also exhibits anti-inflammatory actions in cells, including the inhibition of signaling through STAT1 and STAT3.

Uses

Used in Perfumery:
Dehydrocostus lactone is used as a fragrance ingredient in the perfumery industry due to its unique scent.
Used in Traditional Medicine (Orient):
Dehydrocostus lactone is used as a traditional medicine in the Orient for treating various diseases.
Used in Plant Growth Regulation:
Dehydrocostus lactone is used as a growth regulator in plants, affecting cell viability and cell cycle distribution, which may be useful in addressing drug-resistant tumors.
Used in Anticancer Applications:
Dehydrocostus lactone is used as an anticancer agent, exhibiting diverse anti-cancer properties in cells and animal models. It modulates cell cycle arrest, induces apoptosis, diminishes multidrug resistance, and suppresses angiogenesis in cancer cells.
Used in Drug Delivery Systems:
Dehydrocostus lactone may be employed in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells, potentially improving its delivery, bioavailability, and therapeutic outcomes.

Contact allergens

A guaianolide sesquiterpene lactone extracted from costus oil. It is one of the components of Lactone mix, with costunolide and alantolactone, used to detect Compositae-sensitive patients.

InChI:InChI=1/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1

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Relevant articles and documents

GUAIANE SESQUITERPENES FROM MAGNOLIA WATSONII

The leaves and the trunk barks of Magnolia watsonii afforded two biosynthetic intermediates of dehydrocostuslactone (watsonol A and watsonol B) along with the neolignans, magnolol, honokiol and obovatol, and the aporphine alkaloids, liriodenine and asimilobine.Key Word Index - Magnolia watsonii; Magnoliaceae; sesquiterpenes; dehydrocostuslactone; watsonol A; watsonol B; 15-acetoxycostunolide; neolignans; obovatol; aporphine alkaloids.

Enantioselective Total Synthesis of the Guaianolide (-)-Dehydrocostus Lactone by Enediyne Metathesis

The hydroazulene core of the bioactive sesquiterpenoid (-)-dehydrocostus lactone was generated by domino enediyne metathesis. A triple hydroboration/oxidation of the resultant conjugated triene installed three out of four stereogenic centers of the target in a single step. The enantiopure acyclic metathesis substrate was readily available by an asymmetric anti aldol reaction. Masking of the O-lactone as an acetal allowed for an efficient completion of the synthesis through late-stage double carbonyl olefination.

Guaianolides as immunomodulators. Synthesis and biological activities of dehydrocostus lactone, mokko lactone, eremanthin, and their derivatives

The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from l-α- santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an α-methylene γ- lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.