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CAS Number : 544-64-9
EC Number : 208-876-8
Molecular Formula : C14H26O2
Molecular Weight : 226.35
Preferred IUPAC name :
-(9Z)-Tetradec-9-enoic acid
Other names :
-9-Tetradecenoic acid
-9-cis-Tetradecenoic acid
-cis-Δ9-Tetradecenoic acid
-Myristolenic acid
-Oleomyristic acid
C14:1 Myristoleic Acid, or 9-tetradecenoic acid, is an omega-5 fatty acid.
C14:1 Myristoleic Acid is biosynthesized from myristic acid by the enzyme Stearoyl-CoA desaturase-1, but it is uncommon in nature.
One of the major sources of this fatty acid is the seed oil from plants of the family Myristicaceae, comprising up to 30 per cent of the oil in some species.
C14:1 Myristoleic Acid is a constituent of Serenoa or Saw palmetto, and appears to have activity against LNCaP prostate-cancer cells.
C14:1 Myristoleic Acid is a tetradecenoic acid in which the double bond is at the 9-10 position and has Z configuration.
C14:1 Myristoleic Acid has been isolated from Serenoa repens and has cytotoxic and apoptosis-inducing effects.
C14:1 Myristoleic Acid has a role as an apoptosis inducer, a plant metabolite and an EC 3.1.1.1 (carboxylesterase) inhibitor.
C14:1 Myristoleic Acid is a tetradecenoic acid and a long-chain fatty acid.
C14:1 Myristoleic Acid is a conjugate acid of a myristoleate.
Use and Manufacturing of C14:1 Myristoleic Acid
Industry Uses
-Adhesives and sealant chemicals
-Agricultural chemicals (non-pesticidal)
-Finishing agents
-Lubricants and lubricant additives
-Surface active agents
Consumer Uses
-Adhesives and sealant chemicals
-Agricultural chemicals (non-pesticidal)
Household Products
Household & Commercial/Institutional Products
Information on 2 consumer products that contain Myristoleic acid in the following categories is provided:
-Commercial / Institutional
General Manufacturing Information
Industry Processing Sectors
-All Other Basic Organic Chemical Manufacturing
-Food, beverage, and tobacco product manufacturing
-Miscellaneous Manufacturing
-Paper Manufacturing
-Plastics Product Manufacturing
C14:1 Myristoleic Acid, also known as 9-tetradecenoate or myristoleate, belongs to the class of organic compounds known as long-chain fatty acids.
These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
C14:1 Myristoleic Acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
C14:1 Myristoleic Acid exists in all eukaryotes, ranging from yeast to humans.
Outside of the human body, C14:1 Myristoleic Acid is found in the highest concentration within a few different foods, such as milk (cow), butter, and margarine-like spreads, and in a lower concentration in creams, meat bouillons, and chocolates.
C14:1 Myristoleic Acid has also been detected, but not quantified in, several different foods, such as anchovies, loganberries, sunflowers, yellow zucchinis, and dates.
This could make C14:1 Myristoleic Acid a potential biomarker for the consumption of these foods.
C14:1 Myristoleic Acid is a monounsaturated fatty acid that represents approximately 0.3-0.7% of the total fatty acid composition of adipose tissue triacylglycerol in humans .
C14:1 Myristoleic Acid has been suggested that its effective cytotoxic (i.e. cell death inducer) activity could be used for the treatment of prostate cancer.
C14:1 Myristoleic Acid, or 9-tetradecenoic acid, is an omega-5 fatty acid.
C14:1 Myristoleic Acid 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.
The cetyl ester of C14:1 Myristoleic Acid has biological properties as an anti-inflammatory, a pain reliever, and an immune system modulator.
C14:1 Myristoleic Acid (14 carbon atoms) is an uncommon monounsaturated fatty acid (the cis double bond from the methyl end is omega-5 (ω-5) or n-5, so in shorthand 14:1n-5) member of the sub-group called long chain fatty acids or LCA (from 14 to 18 carbon atoms).
C14:1 Myristoleic Acid is named after the nutmeg (Myristica fragrans).
Nutmeg butter is 75% trimyristin, the triglyceride of myristic acid.
Besides nutmeg, myristic acid is also found in palm oil, butter fat and spermacetin, the crystallized fraction of oil from the sperm whale.
C14:1 Myristoleic Acid is also commonly added co-translationally to the penultimate, nitrogen terminus, glycine in receptor-associated kinases to confer the membrane localisation of the enzyme.
C14:1 Myristoleic Acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.
In this way, C14:1 Myristoleic Acid acts as a lipid anchor in biomembranes.
C14:1 Myristoleic Acid is known as a penetration enhancer for topical preparations.
C14:1 Myristoleic Acid is a waterclear, low viscous oily liquid with a very good spreading capacity on the skin.
C14:1 Myristoleic Acid is mainly used in cosmetics as an oilcomponent for emulsions, bath oils and as a solvent for active substances.
C14:1 Myristoleic Acid is an emollient in cosmetic and pharmaceutical bases.
C14:1 Myristoleic Acid is an emollient, moisturizer, binder, and skin softener that also assists in product penetration.
An ester of myristic acid, C14:1 Myristoleic Acid is naturally occurring in coconut oil and nutmeg.
Although C14:1 Myristoleic Acid is generally considered comedogenic, some ingredient manufacturers clearly specify non-comedogenicity on their data sheets.
C14:1 Myristoleic Acid is a polar emollient and is used in cosmetic and topical pharmaceutical preparations where skin absorption is desired.
C14:1 Myristoleic Acid is also used as a treatment for head lice.
C14:1 Myristoleic Acid is also in flea and tick killing products for pets.
Applications in topical pharmaceutical and cosmetic formulations include bath oils; make-up; hair and nail care products; creams; lotions; lip products; shaving products; skin lubricants; deodorants; otic suspensions; and vaginal creams.
For example, C14:1 Myristoleic Acid is a self-emulsifying component of a proposed cold cream formula, which is suitable for use as a vehicle for drugs or dermatological actives; C14:1 Myristoleic Acid is also used cosmetically in stable mixtures of water and glycerol.
C14:1 Myristoleic Acid is used as a penetration enhancer for transdermal formulations, and has been used in conjunction with therapeutic ultrasound and iontophoresis.
C14:1 Myristoleic Acid has been used in a water-oil gel prolonged-release emulsion and in various microemulsions.
Such microemulsions may increase bioavailability in topical and transdermal applications.
C14:1 Myristoleic Acid has also been used in microspheres, and significantly increased the release of drug from etoposide-loaded microspheres.
C14:1 Myristoleic Acid is used in soft adhesives for pressuresensitive adhesive tapes
C14:1 Myristoleic Acid is colourless liquid of low viscosity
C14:1 Myristoleic Acid is a clear, colorless, practically odorless liquid of low viscosity that congeals at about 5°C.
C14:1 Myristoleic Acid consists of esters of propan-2-ol and saturated high molecular weight fatty acids, principally myristic acid.
C14:1 Myristoleic Acid may be prepared either by the esterification of myristic acid with propan-2-ol or by the reaction of myristoyl chloride and propan-2-ol with the aid of a suitable dehydrochlorinating agent.
C14:1 Myristoleic Acid is used to change the physicochemical characteristics of microsheres such as poly(lactic-co-glycolic acid) (PLGA) microspheres.
C14:1 Myristoleic Acid is used as a oil phase component in the formulaton of microemulsion systems.
Pharmacology:
C14:1 Myristoleic Acid is used in pharmaceutical preparations because Isopropyl myristate improves solubility and increases absorption through the skin.
First Aid Measures of C14:1 Myristoleic Acid
Inhalation:
If inhaled, remove to fresh air.
If breathing becomes difficult, call a physician.
Skin:
Wash with soap and water.
Get medical attention if irritation develops or persists.
Eyes:
Immediately flush with plenty of water.
After initial flushing, remove any contact lenses and continue flushing for at least 15 minutes.
Have eyes examined and tested by medical personnel.
Ingestion:
Wash out mouth with water, keep at rest.
Seek immediate medical attention.
Do NOT induce vomiting unless directed to do so by medical personnel.
Substance identity
EC / List no.: 208-876-8
CAS no.: 544-64-9
Mol. formula: C14H26O2
Hazard classification & labelling of C14:1 Myristoleic Acid
Warning! According to the classification provided by companies to ECHA in CLP notifications this substance causes serious eye irritation, causes skin irritation and may cause respiratory irritation.
C14:1 Myristoleic Acid predicted as likely to meet criteria for category 1A or 1B carcinogenicity, mutagenicity, or reproductive toxicity, or with dispersive or diffuse use(s) where predicted likely to meet any classification criterion for health or environmental hazards, or where there is a nanoform soluble in biological and environmental media.
C14:1 Myristoleic Acid indicated, in 2009, as being intended to be registered by at least one company in the EEA.
C14:1 Myristoleic Acid for which classification and labeling data have been submitted to ECHA in a registration under REACH or notified by manufacturers or importers under CLP.
Such notifications are required for hazardous substances, as such or in mixtures, as well as for all substances subject to registration, regardless of their hazard.
C14:1 Myristoleic Acid listed in the EINECS, ELINCS, or NLP inventories.
Synonyms:
(Z)-tetradec-9-enoic acid
(Z)-tetradec-9-enoic acid
9-Tetradecenoic acid, (9Z)-
(9Z)-tetradec-9-enoic acid
(Z)-Tetradec-9-enoic acid
(Z)-tetradec-9-enoic acid
9-Tetradecenoic acid, (E)-
tetradec-9-enoic acid
544-64-9
Myristoleic acid
544-64-9
(Z)-Tetradec-9-enoic acid
cis-9-tetradecenoic acid
9Z-tetradecenoic acid
9-Tetradecenoic acid, (9Z)-
(9Z)-tetradec-9-enoic acid
9-Tetradecenoic acid
(Z)-9-Tetradecenoicacid
9-Tetradecenoic acid, (Z)-
cis-Delta(9)-tetradecenoic acid
(9Z)-Tetradecenoic acid
CHEMBL456732
RF23WGD123
CHEBI:27781
9-tetradecenoate
9Z-tetradecenoate
cis-9-tetradecenoate
(9Z)-tetradecenoate
cis-Delta(9)-tetradecenoate
Myristolenic acid
Oleomyristic acid
9-cis-Tetradecenoic acid
EINECS 208-876-8
Z-9-Tetradecenoic acid
Z-tetradec-9-enoic acid
cis-tetradec-9-enoic acid
Tetradecenoic acid (cis-9)
UNII-RF23WGD123
(9Z)-9-Tetradecenoic acid
SCHEMBL109270
DTXSID5041568
ZINC4529321
BDBM50269530
LMFA01030051
Myristoleic acid, analytical standard
AKOS037645073
FA 14:1
CIS-.DELTA.9-TETRADECENOIC ACID
AS-56816
FA(14:1(9Z))
Myristoleic acid, >=99% (capillary GC)
HY-113332
CS-0059626
C08322
Q58221
14:1(N-5)
(9Z)-9-Tetradecenoic acid [ACD/IUPAC Name]
(9Z)-9-Tetradecensäure [German] [ACD/IUPAC Name]
(9Z)-Tetradec-9-enoic acid
(9Z)-Tetradecenoic acid
208-876-8 [EINECS]
544-64-9 [RN]
9-Tetradecenoic acid, (9Z)- [ACD/Index Name]
9-Tetradecenoic acid, (Z)-
9Z-tetradecenoic acid
Acide (9Z)-9-tétradécénoïque [French] [ACD/IUPAC Name]
cis-9-Tetradecenoic acid
cis-δ(9)-tetradecenoic acid
MFCD00004436
Myristoleic acid [Wiki]
Myristoleic acid (14:1(n-5))
RF23WGD123
(9Z)-tetradec-9-enoate
(9Z)-Tetradecenoate
(Z)-Tetradec-9-enoate
9-Tetradecenoate [ACD/IUPAC Name]
9Z-tetradecenoate
cis-9-tetradecenoate
cis-δ(9)-tetradecenoate
(Z)-9-Tetradecenoicacid
(Z)-Tetradec-9-enoic acid
1724311 [Beilstein]
198139-51-4 [RN]
CIS-TETRADEC-9-ENOIC ACID
myristoleic acid (9c)
Myristoleic acid 10 ?g/mL in Cyclohexane
Myristoleic Acid|9Z-tetradecenoic acid
Myristolic acid
MYZ
Tetradecenoic acid (cis-9)
Z-9-Tetradecenoic acid
