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lactucin
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))-

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Name:	(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 Number:	1891-29-8	3D/inchi
Other(deleted CASRN):	81241-45-4
FDA UNII:	R6E2918904
Nikkaji Web:	J7.802F
XlogP3-AA:	-0.70 (est)
Molecular Weight:	276.28852000
Formula:	C15 H16 O5
NMR Predictor:	Predict (works with chrome, Edge or firefox)

Category:natural substances and extractives

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:	Search
Google Books:	Search
Google Scholar: with word "volatile"	Search
Google Scholar: with word "flavor"	Search
Google Scholar: with word "odor"	Search
Google Patents:	Search
US Patents:	Search
EU Patents:	Search
Pubchem Patents:	Search
PubMed:	Search
NCBI:	Search

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)

Organoleptic Properties:

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

For experimental / research use only.

Lactucin (HPLC) ≥95%

Safety Information:


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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
natural substances and extractives
Recommendation for lactucin usage levels up to:
	not for fragrance use.

Recommendation for lactucin flavor usage levels up to:
	not for flavor use.

Safety References:

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :442266

National Institute of Allergy and Infectious Diseases:Data

(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

Chemidplus:0001891298

References:

	(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
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	442266
Pubchem (sid):	135247146

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
KEGG (GenomeNet):	C09489
HMDB (The Human Metabolome Database):	HMDB35814
FooDB:	FDB014575
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

Potential Blenders and core components note

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):note

	chicory fruit juice Search Trop Picture
	chicory latex Search Trop Picture
	chicory plant Search Trop Picture
	chicory root Search Trop Picture
	endive Search Trop Picture
	lettuce plant Search Trop Picture

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

Articles:

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].

Notes:

Constit. of Cichorium intybus (chicory) Lactucin is a bitter substance that forms a white crystalline solid and belongs to the group of sesquiterpene lactones. It is found in some varieties of lettuce and is an ingredient of lactucarium. It has been shown to have analgesic and sedative properties.

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