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

Different sources of media describe the Description of 477-43-0 differently. You can refer to the following data:
1. 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.
2. 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

Different sources of media describe the Uses of 477-43-0 differently. You can refer to the following data:
1. Dehydrocostus lactone is the oil extracted from Saussurea lappa is used in perfumery and in the Orient for all kinds of diseases.
2. 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.

Definition

ChEBI: An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone.

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

Upstream product

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Downstream Products

• 126209-82-3 saussureamine B 
• 67667-64-5 3α-hydroxyguaia-4(15),10(14),11(13)-trien-12,6-olide 
• 16838-87-2 zaluzanin C 
• 142808-75-1 3α,5α-dihydroxyguaia-4(15),10(14),11(13)-trien-12,6-olide 
• 4955-03-7 11β,13-dehydrocostuslactone 
• 308789-82-4 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-3-hydroxy-propionic acid 
• 301301-14-4 (R)-2-Amino-3-((3S,3aS,6aR,9aR,9bS)-6,9-dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethylsulfanyl)-propionic acid 
• 308789-80-2 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-4-methyl-pentanoic acid 
• 308789-83-5 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-4-methylsulfanyl-butyric acid 
• 308789-77-7 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-5-guanidino-pentanoic acid 
• 308789-79-9 [((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-acetic acid 
• 872194-91-7 C₁₆H₁₈Br₂O₂ 

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.