EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

falcarinol
panaxynol

Supplier Sponsors

Name:(3R,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol
CAS Number: 21852-80-2Picture of molecule3D/inchi
FDA UNII: 8P1DJD416I
Nikkaji Web:J15.332J
MDL:MFCD00210503
XlogP3-AA:5.50 (est)
Molecular Weight:244.37748000
Formula:C17 H24 O
BioActivity Summary:listing
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: 115.00 °C. @ 102.00 mm Hg
Boiling Point: 368.00 to 370.00 °C. @ 760.00 mm Hg (est)
Flash Point: 326.00 °F. TCC ( 163.40 °C. ) (est)
logP (o/w): 6.257 (est)
Soluble in:
 alcohol
 water, 0.7481 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Falcarinol 70%
BOC Sciences
For experimental / research use only.
Falcarinol > 95%
Odor: characteristic
Use: (R)-(-)-Falcarinol is a covalent cannabinoid (CB1) receptor antagonist that induces pro-allergic effects on skin, and is most commonly found in the extracts of carrots.
 
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 falcarinol usage levels up to:
 not for fragrance use.
 
Recommendation for falcarinol 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 :5281149
National Institute of Allergy and Infectious Diseases:Data
(3R,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol
Chemidplus:0021852802
 
References:
 (3R,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281149
Pubchem (sid):135029349
 
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
CHEMBL:View
KEGG (GenomeNet):C08450
HMDB (The Human Metabolome Database):HMDB39588
FooDB:FDB000702
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 carrot root
Search Trop Picture
 celery root
Search Trop Picture
 falcaria vulgaris
Search Trop Picture
 ivy english ivy
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 parsley leaf oil @ 15.00%
Data GC Search Trop Picture
 parsley root
Search Trop Picture
 schefflera arboricola
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 tomato seed
Search Trop Picture
 
Synonyms:
(3R,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol
1,9-heptadecadiene-4,6-diyn-3-ol
1,9-heptadecadiene-4,6-diyn-3-ol, (3R,9Z)-
 panaxynol
 

Articles:

PubMed:Automated analytical standard production with supercritical fluid chromatography for the quantification of bioactive C17-polyacetylenes: A case study on food processing waste.
PubMed:Polyacetylene levels in carrot juice, effect of pH and thermal processing.
PubMed:Dietary polyacetylenes of the falcarinol type are inhibitors of breast cancer resistance protein (BCRP/ABCG2).
PubMed:Systemic allergic dermatitis caused by Apiaceae root vegetables.
PubMed:Absolute configuration of falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol) from Pastinaca sativa.
PubMed:Variability of the root essential oils of Seseli rigidum Waldst. & Kit. (Apiaceae) from different populations in Serbia.
PubMed:Biosynthesis of panaxynol and panaxydol in Panax ginseng.
PubMed:Quantitative Raman spectroscopy for the analysis of carrot bioactives.
PubMed:Chemical composition and antimicrobial activity of essential oil of different parts of Seseli rigidum.
PubMed:Variation in the volatile constituents of different plant parts of Ligusticopsis wallichiana from western Himalaya, India.
PubMed:Chemical composition and in vitro antimicrobial activity of the essential oil of the flowers of Tridax procumbens.
PubMed:Antitrypanosomal properties of Panax ginseng C. A. Meyer: new possibilities for a remarkable traditional drug.
PubMed:Effects of bioactive compounds from carrots (Daucus carota L.), polyacetylenes, beta-carotene and lutein on human lymphoid leukaemia cells.
PubMed:Anti-mycobacterial diynes from the Canadian medicinal plant Aralia nudicaulis.
PubMed:Polyacetylenes in fresh and stored carrots (Daucus carota): relations to root morphology and sugar content.
PubMed:[Simultaneous determination of panaxynol and panaxydol in fibrous root of Panax ginseng by HPLC].
PubMed:The influence of the fungal pathogen Mycocentrospora acerina on the proteome and polyacetylenes and 6-methoxymellein in organic and conventionally cultivated carrots (Daucus carota) during post harvest storage.
PubMed:Quantification of polyacetylenes in apiaceous plants by high-performance liquid chromatography coupled with diode array detection.
PubMed:Spectroscopic studies on bioactive polyacetylenes and other plant components in wild carrot root.
PubMed:Characterisation of polyacetylenes isolated from carrot (Daucus carota) extracts by negative ion tandem mass spectrometry.
PubMed:Induction of apoptosis in human promyelocytic leukemia HL60 cells by panaxynol and panaxydol.
PubMed:Anticomplement activity of polyacetylenes from leaves of Dendropanax morbifera Leveille.
PubMed:Effect of ultrasound and blanching pretreatments on polyacetylene and carotenoid content of hot air and freeze dried carrot discs.
PubMed:Aliphatic C(17)-polyacetylenes of the falcarinol type as potential health promoting compounds in food plants of the Apiaceae family.
PubMed:Effects of harvesting date and storage on the amounts of polyacetylenes in carrots, Daucus carota.
PubMed:[Inhibition of panaxynol on experimental delayed type hypersensitivity].
PubMed:Comparison of polyacetylene content in organically and conventionally grown carrots using a fast ultrasonic liquid extraction method.
PubMed:Influence of Sous Vide and water immersion processing on polyacetylene content and instrumental color of parsnip (Pastinaca sativa) disks.
PubMed:Dermatitis from common ivy (Hedera helix L. subsp. helix) in Europe: past, present, and future.
PubMed:A new prenylated flavanonol from Seseli annuum roots showing protective effect on human lymphocytes DNA.
PubMed:Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin.
PubMed:Structure determination of bisacetylenic oxylipins in carrots (Daucus carota L.) and enantioselective synthesis of falcarindiol.
PubMed:Panaxynol protects cortical neurons from ischemia-like injury by up-regulation of HIF-1alpha expression and inhibition of apoptotic cascade.
PubMed:Differential effects of falcarinol and related aliphatic C(17)-polyacetylenes on intestinal cell proliferation.
PubMed:Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus.
PubMed:Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
PubMed:Menthol and geraniol biotransformation and glycosylation capacity of Levisticum officinale hairy roots.
PubMed:Biomass and content of ginsenosides and polyacetylenes in American ginseng roots can be increased without affecting the profile of bioactive compounds.
PubMed:Reinvestigation of the bitter compounds in carrots (Daucus carota L.) by using a molecular sensory science approach.
PubMed:The polyacetylenes falcarinol and falcarindiol affect stress responses in myotube cultures in a biphasic manner.
PubMed:Purple carrot (Daucus carota L.) polyacetylenes decrease lipopolysaccharide-induced expression of inflammatory proteins in macrophage and endothelial cells.
PubMed:Antimycobacterial polyacetylenes from Levisticum officinale.
PubMed:Panaxydol and panaxynol protect cultured cortical neurons against Abeta25-35-induced toxicity.
PubMed:Nitrogen stress induction on Levisticum officinale hairy roots grown in darkness and under photoperiod conditions: effect on growth and volatile components.
PubMed:Antiproliferative effect of panaxynol on RASMCs via inhibition of ERK1/2 and CREB.
PubMed:Quantification of two polyacetylenes in Radix Ginseng and roots of related Panax species using a gas chromatography-mass spectrometric method.
PubMed:Determination of polyacetylenes in carrot roots (Daucus carota L.) by high-performance liquid chromatography coupled with diode array detection.
PubMed:Biphasic effect of falcarinol on caco-2 cell proliferation, DNA damage, and apoptosis.
PubMed:Simultaneous determination of ginsenosides and polyacetylenes in American ginseng root (Panax quinquefolium L.) by high-performance liquid chromatography.
PubMed:Structural changes of polyacetylenes in American ginseng root can be observed in situ by using Raman spectroscopy.
PubMed:Protective effect of panaxydol and panaxynol on sodium nitroprusside-induced apoptosis in cortical neurons.
PubMed:Inhibitory effects of coumarin and acetylene constituents from the roots of Angelica furcijuga on D-galactosamine/lipopolysaccharide-induced liver injury in mice and on nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages.
PubMed:Panaxynol induces neurite outgrowth in PC12D cells via cAMP- and MAP kinase-dependent mechanisms.
PubMed:In situ simultaneous analysis of polyacetylenes, carotenoids and polysaccharides in carrot roots.
PubMed:Up-regulation of M1 muscarinic receptors expressed in CHOm1 cells by panaxynol via cAMP pathway.
PubMed:Spatial tissue distribution of polyacetylenes in carrot root.
PubMed:Polyacetylenes from the Apiaceae vegetables carrot, celery, fennel, parsley, and parsnip and their cytotoxic activities.
PubMed:Inhibitory effects of feeding with carrots or (-)-falcarinol on development of azoxymethane-induced preneoplastic lesions in the rat colon.
PubMed:[Allergic contact dermatitis to common ivy (Hedera helix L.)].
PubMed:Lignans, phenylpropanoids and polyacetylenes from Chaerophyllum aureum L. (Apiaceae).
PubMed:Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree.
PubMed:Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction.
PubMed:A tumor cell growth inhibitor from Saposhnikovae divaricata.
PubMed:Occupational allergic contact dermatitis from falcarinol.
PubMed:[GC-MS analysis of essential oils from the roots of Saposhnikovia divaricata (Turcz.) Schischk, Libanotis laticalycina Shan et Sheh, Seseli yunnanense Franch. and Peucedanum dielsianum Fedde ex Wolff].
PubMed:Gymnasterkoreaynes A-F, cytotoxic polyacetylenes from Gymnaster koraiensis.
PubMed:Chemosystematic investigations of irregular diterpenes in Anisotome and related New Zealand Apiaceae.
PubMed:Chemical composition and cytotoxic and antimicrobial activity of Calycotome villosa (Poiret) link leaves.
PubMed:Medicinal foodstuffs. XX. Vasorelaxant active constituents from the roots of Angelica furcijuga Kitagawa: structures of hyuganins A, B, C, and D.
PubMed:Effects of a lipoxygenase inhibitor, panaxynol, on vascular contraction induced by angiotensin II.
PubMed:The allergens of Dendropanax trifidus Makino and Fatsia japonica Decne. et Planch. and evaluation of cross-reactions with other plants of the Araliaceae family.
PubMed:Effect of petroleum ether extract of Panax ginseng roots on proliferation and cell cycle progression of human renal cell carcinoma cells.
PubMed:Hepatoprotective and nitric oxide production inhibitory activities of coumarin and polyacetylene constituents from the roots of Angelica furcijuga.
PubMed:Allergic contact dermatitis from common ivy confirmed with stored allergens.
PubMed:Inhibition of 15-hydroxyprostaglandin dehydrogenase activity in rabbit gastric antral mucosa by panaxynol isolated from oriental medicines.
PubMed:Antiproliferative constituents in Umbelliferae plants II. Screening for polyacetylenes in some Umbelliferae plants, and isolation of panaxynol and falcarindiol from the root of Heracleum moellendorffii.
PubMed:The major allergen of Dendropanax trifidus Makino.
PubMed:Effects of cicutoxin and related polyacetylenes from Cicuta virosa on neuronal action potentials: a comparative study on the mechanism of the convulsive action.
PubMed:Cytotoxic falcarinol oxylipins from Dendropanax arboreus.
PubMed:Effect of non-saponin fraction from Panax ginseng on cGMP and thromboxane A2 in human platelet aggregation.
PubMed:Panaxynol, a polyacetylene compound isolated from oriental medicines, inhibits mammalian lipoxygenases.
PubMed:Bioactive metabolites from Sicilian marine fennel, Crithmum maritimum.
PubMed:The first specific antibody against cytotoxic polyacetylenic alcohol, panaxynol.
PubMed:Cytotoxic activity of polyacetylene compounds in Panax ginseng C. A. Meyer.
PubMed:Isolation, identification, and bioassay of chemicals affecting nonpreference carrot-root resistance to carrot-fly larva.
PubMed:Antiplatelet actions of panaxynol and ginsenosides isolated from ginseng.
PubMed:Human maximization test of falcarinol, the principal contact allergen of English ivy and Algerian ivy (Hedera helix, H. canariensis).
PubMed:[Chemical studies on crude drug processing. V. On the constituents of ginseng radix rubra (2): Comparison of the constituents of white ginseng and red ginseng prepared from the same Panax ginseng root].
PubMed:Allergic and irritant contact dermatitis from falcarinol and didehydrofalcarinol in common ivy (Hedera helix L.).
PubMed:Allergic contact dermatitis from falcarinol isolated from Schefflera arboricola.
PubMed:In vitro effect of Panax ginseng on phytohaemagglutinin-induced lymphocyte transformation.
PubMed:[Chemical studies of crude drugs (1). Constituents of Ginseng radix rubra].
PubMed:[Studies on anti-inflammatory agents. IV. Anti-inflammatory constituents from roots of Panax ginseng C.A. Meyer (author's transl)].
PubMed:High-pressure liquid chromatographic separation of the naturally occurring toxicants myristicin, related aromatic ethers and falcarinol.
PubMed:Analysis of myristicin and falcarinol in carrots by high-pressure liquid chromatography.
PubMed:Anti-nociceptive substances from the roots of Angelica acutiloba.
 
Notes:
an acetylenic hydrocarbon, similar to cicutoxin, derived from oleic acid in araliaceae, umbelliferae and other plants; it can cause contact dermatitis in some individuals; panaxynol is the 3,4-cis-8,9-trans isomer of falcarinol. Isol. from ginseng
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