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

(Z)-9-tetradecenoic acid
myristoleic acid

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Name:(Z)-tetradec-9-enoic acid
CAS Number: 544-64-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-876-8
Nikkaji Web:J11.362J
XlogP3:5.10 (est)
Molecular Weight:226.35962000
Formula:C14 H26 O2
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
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 338.00 to 339.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000017 mmHg @ 25.00 °C. (est)
Flash Point: 404.00 °F. TCC ( 206.50 °C. ) (est)
logP (o/w): 5.383 (est)
Soluble in:
 water, 0.9431 mg/L @ 25 °C (est)
Insoluble in:
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
BOC Sciences
For experimental / research use only.
Santa Cruz Biotechnology
For experimental / research use only.
Myristoleic acid
Sigma-Aldrich: Sigma
For experimental / research use only.
Myristoleic acid ≥99% (capillary GC)
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
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:
natural substances and extractives
Recommendation for (Z)-9-tetradecenoic acid usage levels up to:
 not for fragrance use.
Recommendation for (Z)-9-tetradecenoic acid flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):544-64-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281119
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(Z)-tetradec-9-enoic acid
 (Z)-tetradec-9-enoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:544-64-9
Pubchem (cid):5281119
Pubchem (sid):135024344
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
KEGG (GenomeNet):C08322
HMDB (The Human Metabolome Database):HMDB02000
YMDB (Yeast Metabolome Database):YMDB00680
Export Tariff Code:2916.19.3000
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 buckwheat pollen
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 carrot seed
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 dandelion pollen
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 papaya flower
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 papaya fruit
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 poppy opium poppy seed oil
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 ziziphus jujuba
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 myristoleic acid
(9Z)-tetradec-9-enoic acid
(Z)-tetradec-9-enoic acid
cis-tetradec-9-enoic acid
(9Z)-tetradecenoic acid
(9Z)-9-tetradecenoic acid
cis-9-tetradecenoic acid
9-tetradecenoic acid, (9Z)-
9-tetradecenoic acid, (Z)-


PubMed:Malva verticillata seed extracts upregulate the Wnt pathway in human dermal papilla cells.
PubMed:System model network for adipose tissue signatures related to weight changes in response to calorie restriction and subsequent weight maintenance.
PubMed:Comparing the fatty acid levels of preterm and term breast milk in Turkish women.
PubMed:Reconciling ligase ribozyme activity with Fatty Acid vesicle stability.
PubMed:Polymorphisms in lipogenic genes and milk fatty acid composition in Holstein dairy cattle.
PubMed:Fatty Acid and Volatile Oil Compositions of Allomyrina dichotoma Larvae.
PubMed:Metabolomic analysis of cold acclimation of Arctic Mesorhizobium sp. strain N33.
PubMed:Identification of some yeasts by fatty acid profiles.
PubMed:Oxyfunctionalization of aliphatic compounds by a recombinant peroxygenase from Coprinopsis cinerea.
PubMed:Ileal flows and apparent ileal digestibility of fatty acids in growing gilts fed flaxseed containing diets.
PubMed:Seasonal changes of buffalo colostrum: physicochemical parameters, fatty acids and cholesterol variation.
PubMed:Multivariate data analysis for finding the relevant fatty acids contributing to the melting fractions of cream.
PubMed:Association of five candidate genes with fatty acid composition in Korean cattle.
PubMed:Production of 10-hydroxystearic acid from oleic acid and olive oil hydrolyzate by an oleate hydratase from Lysinibacillus fusiformis.
PubMed:Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces avermitilis.
PubMed:Biosynthesis of the pyoverdine siderophore of Pseudomonas aeruginosa involves precursors with a myristic or a myristoleic acid chain.
PubMed:Regioselective oxygenation of fatty acids, fatty alcohols and other aliphatic compounds by a basidiomycete heme-thiolate peroxidase.
PubMed:Effects of bovine fatty acid synthase, stearoyl-coenzyme A desaturase, sterol regulatory element-binding protein 1, and growth hormone gene polymorphisms on fatty acid composition and carcass traits in Japanese Black cattle.
PubMed:Free fatty acids profile of the fetal brain and the plasma, liver, brain and kidneys of pregnant rats treated with sodium arsenite at mid-organogenesis.
PubMed:Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy.
PubMed:Striatal dopamine in the response of brain and liver unsaturated and saturated free fatty acids following administration of C75 in CD-1 mice.
PubMed:Stearoyl-CoA desaturase 1 genotype and stage of lactation influences milk fatty acid composition of Canadian Holstein cows.
PubMed:Biochemical composition of some red and brown macro algae from the Northeastern Mediterranean Sea.
PubMed:Lipid compounds of the umbilical cord vein and their alterations in preeclampsia.
PubMed:Effect of a seaweed extract on fatty acid accumulation and glycerol-3-phosphate dehydrogenase activity in 3T3-L1 adipocytes.
PubMed:Purification and identification of bovine cheese whey fatty acids exhibiting in vitro antifungal activity.
PubMed:Measurements of binary diffusion coefficients, retention factors and partial molar volumes for myristoleic acid and its methyl ester in supercritical carbon dioxide.
PubMed:Whey-derived free fatty acids suppress the germination of Candida albicans in vitro.
PubMed:RNA catalysis in model protocell vesicles.
PubMed:Sulfoquinovosylmonoacylglycerol inhibitory mode analysis of rat DNA polymerase beta.
PubMed:The effects of topical application of various fatty acids on pheromone and glandular lipid biosynthesis in the moth Heliothis virescens.
PubMed:Fusion of lamellar body with plasma membrane is driven by the dual action of annexin II tetramer and arachidonic acid.
PubMed:Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.
PubMed:Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells.
PubMed:Breed effects on growth performance, carcass characteristics, fatty acid composition, and palatability attributes in finishing steers.
PubMed:Chimeras of Delta6-fatty acid and Delta8-sphingolipid desaturases.
PubMed:Elo1p-dependent carboxy-terminal elongation of C14:1Delta(9) to C16:1Delta(11) fatty acids in Saccharomyces cerevisiae.
PubMed:Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue.
PubMed:Enhancement of propylene glycol distribution in the skin by high purity cis-unsaturated fatty acids with different alkyl chain lengths having different double bond position.
PubMed:Thiazolidinediones downregulate stearoyl-CoA desaturase 1 gene expression in 3T3-L1 adipocytes.
PubMed:Stimulatory effect of fatty acid treatment on glucose utilization in human erythrocytes.
PubMed:The inhibitory action of fatty acids on oral bacteria.
PubMed:Production of 10-Ketostearic Acid from Oleic Acid by Flavobacterium sp. Strain DS5 (NRRL B-14859).
PubMed:Type A behavior and adipose tissue linoleic acid: implications for stress management.
PubMed:Cetyl myristoleate isolated from Swiss albino mice: an apparent protective agent against adjuvant arthritis in rats.
PubMed:[The effect of zinc depletion on the fat content and fatty acid composition of the liver and brain in forcibly fed rats].
PubMed:Inhibition of steroid 5 alpha-reductase by specific aliphatic unsaturated fatty acids.
PubMed:Effect of modification of HEp 2 cell membrane lipidic phase on susceptibility to infection from herpes simplex virus.
PubMed:Rapid determination by high-performance liquid chromatography of free fatty acids released from rat platelets after derivatization with monodansylcadaverine.
PubMed:Regulation of transmembrane ion transport by reaction products of phospholipase A2. II. Effects of arachidonic acid and other fatty acids on mitochondrial Ca2+ transport.
PubMed:Induction of the differentiation of HL-60 promyelocytic leukemia cells by palmitoleic and myristoleic acids.
PubMed:Certain physiochemical properties of uterine tubal fluid, follicular fluid, and blood plasma in the mare.
PubMed:Effect of diethylstilboestrol on adipose-tissue lipids.
Occurs in natural fats, e.g. Cottonseed oil Myristoleic acid is a monounsaturated fatty acid that represent approximately 0.3 - 0.7% of the total fatty acid composition of adipose tissue triacylglycerol in human. (PMID 10393134); It has been suggested that his cytotoxic and effective cell death inducer activity could be used for the treatment of prostate cancer. (PMID 11304730); Myristoleic acid, or 9-tetradecenoic acid, is an omega-5 fatty acid. It is biosynthesized from myristic acid by the enzyme delta-9 desaturase, but it is uncommon in nature. One of the major sources of this fatty acid is the seed oil from plants of the genus Myristicaceae, comprising up to 30 per cent of the oil in some species.
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