9-tetradecenoic acid
myristelaidic acid
 
Notes:
None found
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CAS Number: 13147-06-3Picture of molecule3D/inchi
XlogP3: 5.10 (est)
Molecular Weight: 226.35962000
Formula: C14 H26 O2
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
Soluble in:
 water, 0.9431 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:
 None found
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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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 9-tetradecenoic acid usage levels up to:
 not for fragrance use.
 
Recommendation for 9-tetradecenoic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 68344
National Institute of Allergy and Infectious Diseases: Data
 tetradec-9-enoic acid
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References:
 tetradec-9-enoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 68344
Pubchem (sid): 43124934
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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
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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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
 found in nature
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Synonyms:
 myristelaidic acid
 tetradec-9-enoic acid
 tetradecenoic acid, 9-
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Articles:
PubMed: Automated pathway and reaction prediction facilitates in silico identification of unknown metabolites in human cohort studies.
PubMed: Alkenyl Carboxylic Acid: Engineering the Nanomorphology in Polymer-Polymer Solar Cells as Solvent Additive.
PubMed: Meat quality of lambs fed diets with peanut cake.
PubMed: Myristoylation increases the CD8+T-cell response to a GFP prototype antigen delivered by modified vaccinia virus Ankara.
PubMed: Myristoleic acid inhibits osteoclast formation and bone resorption by suppressing the RANKL activation of Src and Pyk2.
PubMed: Hydrogen Exchange Mass Spectrometry of Proteins at Langmuir Monolayers.
PubMed: Membrane-Associated Conformation of HIV-1 Nef Investigated with Hydrogen Exchange Mass Spectrometry at a Langmuir Monolayer.
PubMed: Efficient demyristoylase activity of SIRT2 revealed by kinetic and structural studies.
PubMed: Successful management of pregnancy with very-long-chain acyl-coenzyme A dehydrogenase deficiency.
PubMed: The HIV-1 Pr55 gag polyprotein binds to plastidial membranes and leads to severe impairment of chloroplast biogenesis and seedling lethality in transplastomic tobacco plants.
PubMed: In vitro myristoylation assay of Arabidopsis proteins.
PubMed: Exploitation of eukaryotic subcellular targeting mechanisms by bacterial effectors.
PubMed: Dietary intake of specific fatty acids and breast cancer risk among postmenopausal women in the VITAL cohort.
PubMed: Fatty acid composition of adipose tissue triglycerides after weight loss and weight maintenance: the DIOGENES study.
PubMed: Structural basis for Arl3-specific release of myristoylated ciliary cargo from UNC119.
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: Computational analysis and structure predictions of CHH-related peptides from Litopenaeus vannamei.
PubMed: Sunitinib induces apoptosis and growth arrest of medulloblastoma tumor cells by inhibiting STAT3 and AKT signaling pathways.
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: Key biosynthetic gene subfamily recruited for pheromone production prior to the extensive radiation of Lepidoptera.
PubMed: Aspergillus nidulans ArfB plays a role in endocytosis and polarized growth.
PubMed: Dual fatty acyl modification determines the localization and plasma membrane targeting of CBL/CIPK Ca2+ signaling complexes in Arabidopsis.
PubMed: Unexpected tails of a Ca2+ sensor.
PubMed: Peptides modified by myristoylation activate eNOS in endothelial cells through Akt phosphorylation.
PubMed: Sulfoquinovosylmonoacylglycerol inhibitory mode analysis of rat DNA polymerase beta.
PubMed: The nuclear lamina in Heidelberg and Würzburg: a personal view.
PubMed: Expression and evolution of delta9 and delta11 desaturase genes in the moth Spodoptera littoralis.
PubMed: The emergence of competition between model protocells.
PubMed: Antagonizing potencies of saturated and unsaturated long-chain free fatty acids to isoflurane in goldfish.
PubMed: The effects of topical application of various fatty acids on pheromone and glandular lipid biosynthesis in the moth Heliothis virescens.
PubMed: Experimental models of primitive cellular compartments: encapsulation, growth, and division.
PubMed: PACE-1, a novel protein that interacts with the C-terminal domain of ezrin.
PubMed: Exogenous myristoylated-G(i2)alpha subunits of GTP-binding proteins are mitogens following their internalization by astrocytes in culture.
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: Different properties of two isoforms of annexin XIII in MDCK cells.
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: Tissue stores of individual monounsaturated fatty acids and breast cancer: the EURAMIC study. European Community Multicenter Study on Antioxidants, Myocardial Infarction, and Breast Cancer.
PubMed: Biosynthetic pathway for producing the sex pheromone component (Z,E)-9,12-tetradecadienyl acetate in moths involves a delta 12 desaturase.
PubMed: Characterization of a structurally and functionally diverged acyl-acyl carrier protein desaturase from milkweed seed.
PubMed: Stimulatory effect of fatty acid treatment on glucose utilization in human erythrocytes.
PubMed: Binding of hisactophilin I and II to lipid membranes is controlled by a pH-dependent myristoyl-histidine switch.
PubMed: A diet containing myristoleic plus palmitoleic acids elevates plasma cholesterol in young growing swine.
PubMed: Type A behavior and adipose tissue linoleic acid: implications for stress management.
PubMed: Induction of the differentiation of HL-60 promyelocytic leukemia cells by palmitoleic and myristoleic acids.
PubMed: Fatty acid composition of thermophilic, mesophilic, and psychrophilic clostridia.
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