azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, (3aR-(3aalpha,4beta,9aalpha,9bbeta))-

CAS: 1891-29-8 C15 H16 O5 MW: 276.28852000

Identification

Namelactucin
IUPAC(3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
CAS Number1891-29-8
FDA UNIIR6E2918904
Molecular FormulaC15 H16 O5
Molecular Weight276.28852000
Nikkaji NumberJ7.802F

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 575.60 °C. @ 760.00 mm Hg (est)
Flash Point 431.00 °F. TCC ( 221.70 °C. ) (est)
logP (o/w) 0.330 (est)
Soluble in water, 7.107e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for lactucin usage levels up tonot for fragrance use.
Recommendation for lactucin flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

None Found

Natural Occurrence

chicory fruit juice chicory latex chicory plant chicory root endive lettuce plant

Synonyms

azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylene-, (3aR-(3aalpha,4beta,9aalpha,9bbeta))- (3aR,4S,9aS,9bR)-4- hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione lactucine PubMed: Chemotaxonomic value of magastigmane glucosides of Cichorium calvum. PubMed: Regulation of 3β-hydroxysteroid dehydrogenase and sulphotransferase 2A1 gene expression in primary porcine hepatocytes by selected sex-steroids and plant secondary metabolites from chicory (Cichorium intybus L.) and wormwood (Artemisia sp.). PubMed: Regulation of cytochrome P450 mRNA expression in primary porcine hepatocytes by selected secondary plant metabolites from chicory (Cichorium intybus L.). PubMed: Reversed-phase ultra-high-performance liquid chromatography coupled to electrospray ionization-quadrupole-time-of-flight mass spectrometry as a powerful tool for metabolic profiling of vegetables: Lactuca sativa as an example of its application. PubMed: Terpenoids from Cichorium intybus. PubMed: Introducing Cichorium Pumilum as a potential therapeutical agent against drug-induced benign breast tumor in rats. PubMed: Complete NMR spectral assignments of two lactucin-type sesquiterpene lactone glycosides from Picris conyzoides. PubMed: In vitro analysis of the anthelmintic activity of forage chicory (Cichorium intybus L.) sesquiterpene lactones against a predominantly Haemonchus contortus egg population. PubMed: [Comparative studies in content of major active compositions in different parts of Cichorium glandulosum]. PubMed: 11β,13-Dihydro-lactucin-8-O-acetate hemihydrate. PubMed: Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. PubMed: Lignans and sesquiterpenoids from Lactuca sibirica. PubMed: Isolation of three sesquiterpene lactones from the roots of Cichorium glandulosum Boiss. et Huet. by high-speed counter-current chromatography. PubMed: Triterpenoids and Sesquiterpenes from Mulgedium tataricum. PubMed: Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice. PubMed: Influence of cultivation site on sesquiterpene lactone composition of forage chicory (Cichorium intybus L.). PubMed: Two new sesquiterpene lactones from Ixeris chinensis. PubMed: Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L. PubMed: Root constituents of Cichorium pumilum and rearrangements of some lactucin-like guaianolides. PubMed: Chemical stimulants of leaf-trenching by cabbage loopers: natural products, neurotransmitters, insecticides, and drugs. PubMed: Cloning and expression of sesquiterpene synthase genes from lettuce (Lactuca sativa L.). PubMed: Hypoglycemic effects of lactucin-8-O-methylacrylate of Parmentiera edulis fruit. PubMed: Metabolite profiling of sesquiterpene lactones from Lactuca species. Major latex components are novel oxalate and sulfate conjugates of lactucin and its derivatives. PubMed: (+)-Germacrene A biosynthesis . The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory PubMed: Guaianolides from Lactuca saligna. PubMed: [Studies on the photochemical transformation of lactucin]. PubMed: [Research on the preparation of lactucin and lactucopicrin from Lactuca virosa plants. 15. On the enzymatic and non-enzymatic oxidation of therapeutically active plant substances].