74299-48-2

Basic information

• Product Name: Dehydrocostuslactone
• Synonyms: Decahydro-3,6,9-tris(methylene)azuleno[4,5-b]furan-2(3H)-one;Dehydrocostuslactone
• CAS NO: 74299-48-2
• Molecular Formula: C₁₅H₁₈O₂
• Molecular Weight: 230.3
• Mol File: 74299-48-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 383.7 °C at 760 mmHg
• Flash Point: 161.2 °C
• Appearance: white powder
• Density: 1.09
• Vapor Pressure: 4.31E-06mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: Dehydrocostuslactone(CAS DataBase Reference)
• NIST Chemistry Reference: Dehydrocostuslactone(74299-48-2)
• EPA Substance Registry System: Dehydrocostuslactone(74299-48-2)

Safety Data

• Hazardous Substances Data: 74299-48-2(Hazardous Substances Data)

Usage

General Description

Dehydrocostuslactone, also known as DLC, is a natural sesquiterpene lactone found in several medicinal plants. It has been reported to possess various biological activities, including anti-inflammatory, choleretic, anti-malarial, and antitumor effects. DLC has been studied for its potential as a therapeutic agent in the treatment of various diseases, including cancer, inflammatory disorders, and liver diseases. It has shown promising results in preclinical studies as a potential candidate for the development of new drugs. The compound's beneficial effects are attributed to its ability to modulate various signaling pathways and exert antioxidant and anti-inflammatory effects, making it a potential target in drug discovery and development.

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

• 90807-55-9 (3R,3aR,6aR,9aR,9bR)-3-Methyl-6,9-dimethylene-3-phenylselanyl-decahydro-azuleno[4,5-b]furan-2-one 
• 90548-06-4 watsonol A 
• 126209-82-3 saussureamine B 
• 308789-79-9 [((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-acetic acid 
• 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 
• 308789-81-3 (S)-2-[((3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-2-oxo-dodecahydro-azuleno[4,5-b]furan-3-ylmethyl)-amino]-3-phenyl-propionic 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 
• 60134-10-3 1-oxo-eudesm-2,4(15)-dien-5α,6β,7α,11βH-12,6-olide 
• 32223-12-4 11β,13-dihydroreynosin 
• 58698-14-9 1-oxo-Δ²-santenolide 
• 66321-33-3 1-oxo-eudesm-4(15)-en-5α,6β,7α,11βH-12,6-olide 

Downstream Products

• 22419-86-9 (3R)-6,9-bis-methylene-(3rN,3at,6at,9at,9bc)-Δ^1'-dodecahydro-spiro[azuleno[4,5-b]furan-3,3'-pyrazol]-2-one 
• 68151-26-8 isodehydrocostus lactone 
• 143246-39-3 4α-Methoxydehydrocostus lactone 
• 143246-38-2 4β-Methoxydehydrocostus lactone 
• 142506-58-9 5α-hydroxy-isozaluzanin C 
• 16838-87-2 3α-hydroxyguaia-4(15),10(14),11(13)-trien-6,12-olide 
• 142138-73-6 13-Benzoylcostuslactone 
• 67667-64-5 3α-hydroxyguaia-4(15),10(14),11(13)-trien-12,6-olide 
• 106533-13-5 13-hydroxycostuslactone 
• 130518-92-2 (3aS,9bS)-6,9-Dimethylene-3-(2-oxo-propyl)-decahydro-azuleno[4,5-b]furan-2-one 
• 142138-71-4 (3R,3aS,6aR,9aR,9bS)-6,9-Dimethylene-3-(2-oxo-propyl)-decahydro-azuleno[4,5-b]furan-2-one 
• 142138-72-5 (3R,3aS,6aR,9aR,9bS)-3-(2-Hydroxy-propyl)-6,9-dimethylene-decahydro-azuleno[4,5-b]furan-2-one 
• 126209-82-3 saussureamine B 
• 213821-55-7 C₁₅H₁₈O₃ 

Relevant articles and documents

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.

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

From the methanolic extract of the dried roots of Saussurea lappa Clarke, Saussureae Radix, five amino acid-sesquiterpene conjugates, saussureamines A, B, C, D and E, were isolated together with a lignan glycoside, (-)-massoniresinol 4-O-β-D-glucopyranoside. Their stereostructures were determined on the basis of chemical and physicochemical evidence. In addition, saussureamines and the related amino acid-sesquiterpene conjugates were synthesized using a Michael type addition reaction of amino acid to the α-methylene-γ-lactone moiety of sesquiterpenes. Saussureamines A, B and C, costunolide and dehydrocostus lactone showed a gastroprotective effect on acidified ethanol-induced gastric mucosal lesions in rats. Saussureamines A also exhibited an inhibitory effect on gastric mucosal lesions induced by water-immersion stress in mice. (C) 2000 Elsevier Science Ltd.

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.