germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha,8-alpha,15-trihydroxy-, 12,6-lactone, 8-(3,4-dihydroxy-2-methylenebutyrate)

CAS: 24394-09-0 C20 H26 O7 MW: 378.42162000

Identification

Namecnicin
IUPAC[(3aR,4S,6Z,10E,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate
CAS Number24394-09-0
EINECS246-221-8
FDA UNIIC998MWY30L
Molecular FormulaC20 H26 O7
Molecular Weight378.42162000
MDL NumberMFCD00075707

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 143.00 °C. @ 760.00 mm Hg
Boiling Point 622.30 °C. @ 760.00 mm Hg (est)
Flash Point 426.00 °F. TCC ( 219.10 °C. ) (est)
logP (o/w) 2.320 (est)
Soluble in water, 714.8 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral Toxicityoral-mouse LD50 452 mg/kg
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

No supplier data available

Potential Uses

None Found

Natural Occurrence

thistle holy thistle

Synonyms

cnicine germacra-1(10),4,11(13)-trien-12-oic acid, 6-alpha,8-alpha,15-trihydroxy-, 12,6-lactone, 8-(3,4-dihydroxy-2-methylenebutyrate) [(3aR,4S,6Z,10E,11aR)-10-( hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate 2,3,3a,4,5,8,9,11a- octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca(b)furan-4-yl 3,4-dihydroxy-2-methylenebutyrate PubMed: Sesquiterpene lactones from Centaurea zuccariniana and their antimicrobial activity. PubMed: Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. PubMed: Antimyeloma activity of the sesquiterpene lactone cnicin: impact on Pim-2 kinase as a novel therapeutic target. PubMed: Secondary metabolites of Centaurea calolepis and evaluation of cnicin for anti-inflammatory, antioxidant, and cytotoxic activities. PubMed: Antibacterial and cytotoxic activities of the sesquiterpene lactones cnicin and onopordopicrin. PubMed: Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria. PubMed: Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA. PubMed: Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide. PubMed: The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship. PubMed: The unusual binding mode of cnicin to the antibacterial target enzyme MurA revealed by X-ray crystallography. PubMed: Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA. PubMed: Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus). PubMed: Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities. PubMed: Antibacterial evaluation of cnicin and some natural and semisynthetic analogues. PubMed: New sources and antifungal activity of sesquiterpene lactones. PubMed: Microbial transformation of sesquiterpene lactones by the fungi cunninghamella echinulata and rhizopus oryzae PubMed: Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana. PubMed: Sesquiterpene lactones and other constituents of Centaurea napifolia. PubMed: Influence of cnicin, a sesquiterpene lactone ofCentaurea maculosa (Asteraceae), on specialist and generalist insect herbivores. PubMed: [Analysis and action of cnicin]. PubMed: Phytotoxic properties of cnicin, a sesquiterpene lactone fromcentaurea maculosa (spotted knapweed). PubMed: [Further Compounds from Centaurea stoebe.]. PubMed: Sesquiterpene Lactones from Aegialophila pumila. PubMed: [Antibiotic and cytotoxic activity of cnicin and of its hydrolysis products. Chemical structure - biological activity relationship (author's transl)]. PubMed: [Antibiotic and cytotoxic activity of cnicin isolated from Cnicus benedictus L].