cnicin
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)
 
Notes:
extract from cnicus benedictus.
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CAS Number: 24394-09-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 246-221-8
FDA UNII: C998MWY30L
MDL: MFCD00075707
XlogP3-AA: 0.20 (est)
Molecular Weight: 378.42162000
Formula: C20 H26 O7
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Carbosynth
For experimental / research use only.
Cnicin
ExtraSynthese
For experimental / research use only.
Cnicin (HPLC) ≥90%
Santa Cruz Biotechnology
For experimental / research use only.
Cnicin
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50  452 mg/kg
Planta Medica. Vol. 53, Pg. 247, 1987.

intraperitoneal-mouse LDLo  25 mg/kg
Planta Medica. Vol. 29, Pg. 179, 1976.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
 
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 6436586
National Institute of Allergy and Infectious Diseases: Data
 [(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
Chemidplus: 0024394090
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References:
 [(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
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 6436586
Pubchem (sid): 135047846
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
EFSA Update of results on the monitoring of furan levels in food: Read Report
EFSA Previous report: Results on the monitoring of furan levels in food: Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food: Read Report
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 thistle holy thistle
Search Trop  Picture
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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
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Articles:
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].
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