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CAS Number : 373-49-9
EC Number : 206-765-9
ECHA InfoCard : 100.006.151
PubChem CID : 445638
Chemical formula : C16H30O2
Molar mass : 254.414 g·mol−1
Density : 0.894 g/cm3
Melting point : −0.1 °C
Preferred IUPAC name :
-(9Z)-Hexadec-9-enoic acid
Other names :
-Palmitoleic acid
-cis-Palmitoleic acid
-9-cis-Hexadecenoic acid
-C16:1 (Lipid numbers)
C16:1 Palmitoleic is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue.
C16:1 Palmitoleic is present in all tissues but, in general, found in higher concentrations in the liver.
C16:1 Palmitoleic is biosynthesized from palmitic acid by the action of the enzyme Stearoyl-CoA desaturase-1.
Animal and cell culture studies indicate that palmitoleic acid is anti-inflammatory, and improves insulin sensitivity in liver and skeletal muscles, but more studies are required to establish its actions in humans.
Many of the effects of C16:1 Palmitoleic are due to its activation of PPAR-alpha.
Dietary sources of C16:1 Palmitoleic
C16:1 Palmitoleic can be abbreviated as 16:1∆9.
Dietary sources of C16:1 Palmitoleic include breast milk, a variety of animal fats, vegetable oils, and marine oils.
Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources with high concentrations, containing 17% and 19-29% palmitoleic acid, respectively.
C16:1 Palmitoleic is a hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration.
C16:1 Palmitoleic has a role as an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia galeata metabolite, a human blood serum metabolite, an algal metabolite and an Escherichia coli metabolite.
C16:1 Palmitoleic is a conjugate acid of a palmitoleate.
C16:1 Palmitoleic is an important fatty acid for pharmaceutical applications.
C16:1 Palmitoleic is postulated to have anti-thrombotic effects, which can help prevent stroke .
At present, C16:1 Palmitoleic is mainly obtained from Macadamia oil (Macadamia integrifolia), which contains ∼17% palmitoleic acid.
C16:1 Palmitoleic is produced by desaturation of palmitic acid.
C16:1 Palmitoleic is envisaged that Δ9-stearoyl-ACP desaturase, which acts mainly on stearic acid, can also use palmitic acid as substrate to produce C16:1 Palmitoleic.
Several mutant stearoyl-ACP desaturases with increased specificity towards palmitoyl-ACP have been created and have been demonstrated to drive high levels of C16:1 Palmitoleic synthesis in Arabidopsis.
C16:1 Palmitoleic is often found as a component of human adipose tissues, esterified to glycerol.
C16:1 Palmitoleic is synthesized from palmitic acid by the enzyme delta-9- desaturase.
C16:1 Palmitoleic can therefore be an indicator of de novo fatty acid synthesis.
C16:1 Palmitoleic has been reported that there is a consistant positive association which changes in inflammatory markers and palmitoleic acid.
C16:1 Palmitoleic , 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.
Based on a literature review a significant number of articles have been published on C16:1 Palmitoleic .
C16:1 Palmitoleic is typically found in ruminant-derived foods (milk and meat).
Of note, previous epidemiological studies associated high levels of circulating C16:1 Palmitoleic with a lower risk of type 2 diabetes and metabolic syndrome in humans.
Application of C16:1 Palmitoleic
This analytical standard can also be used as follows:
-Simultaneous identification and quantification of fatty acids from blood plasma samples after their methyl derivatization by large-volume injection (LVI) gas chromatography combined with vacuum ultraviolet spectroscopy (GC-VUV)
-Multi-residue analysis of oleic acid and other related fatty acids using a derivatization-free method based on gas chromatography-flame ionization detection (GC-FID)
-Comparative evaluation of high-performance liquid chromatography (HPLC) and gas chromatography (GC) methods for the determination of cis- and trans- palmitoleic acids in fish oil samples, using a modified potassium hydroxide ester exchange method
-Separation and determination of fatty acids by gas chromatography (GC) and amino acids by ultra-fast liquid chromatography-ultraviolet (UFLC-UV) detection from goldband goatfish harvested during different seasons
-Development of a liquid chromatography-mass spectrometry (LC-MS) method to measure seven fatty acid esters of hydroxy fatty acids (FAHFAs), four fatty acids, and four cardiovascular-related biomarkers in plasma samples of 57 healthy individuals
C16:1 Palmitoleic is commonly found in dairy products.
Previous epidemiological work associated C16:1 Palmitoleic with lower risk of metabolic syndrome.
To date however, no nutritional study exists to verify such hypothesis, mostly due to the low availability of C16:1 Palmitoleic.
C16:1 Palmitoleic is isomers of palmitoleic acid, a monounsaturated fatty acid which affects glucose and lipid metabolism, and reduces insulin resistance.
C16:1 Palmitoleic is used as a biomarker for indicating the risk of type II diabetes and coronary heart disease, but no methods of analysis or distinguishing between cis-POA and trans-POA have yet been reported.
C16:1 Palmitoleic, a monounsaturated fatty acid which could affect glucose and lipid metabolism and reduce insulin resistance has two isomers, i.e. cis-palmitoleic acid (cPOA) and trans-palmitoleic acid (tPOA).
C16:1 Palmitoleic is widely used as a raw material for production of various esters, fatty alcohols, fatty acid isethionates, metallic soaps, fatty acid sarcosinates, imidazolines, fatty amines, oxazolines, surfactants in personal care products, liquid and transparent soaps, corrosion/rust inhibitor for antifreeze.
C16:1 Palmitoleic is used in agricultural chemicals, food, adhesive, crayon, candles, cements, coatings, inks, leather waxes, lubricants, metal workings, mining, pencils, capsules and ointments, plastics, rubber, textiles etc.
C16:1 Palmitoleic is one of the most common saturated fatty acids and one of the most common in body lipids: C16:1 Palmitoleic accounts for 21 to 30% of human fat tissue (fat).
C16:1 Palmitoleic is found in both animals and plants, mainly from palm oil (hence Palmitic Acid name).
C16:1 Palmitoleic is most commonly produced from palm oil, although C16:1 Palmitoleic is found in smaller amounts in other vegetable oils as well as dairy and meat.
To produce pure C16:1 Palmitoleic, the oil is boiled to break the fatty acids off of the glycerol and then the different acids are separated out based on their boiling point.
As a fatty acid, C16:1 Palmitoleic can act as an emollient.
When applied to the skin by lotions, creams or bath oils, emollients can soften the skin and help C16:1 Palmitoleic retain moisture by forming an oily, water blocking layer that slows the loss of water through the skin.
This can improve dry and flaky skin as well as conditions like psoriasis and eczema.
C16:1 Palmitoleic is a saturated fat.
C16:1 Palmitoleic’s naturally found in some animal products like meat and dairy, as well as in palm and coconut oils.
Because these two oils are frequently used in processed foods, you might be getting palmitic acid in your diet without even realizing C16:1 Palmitoleic.
In cosmetics, C16:1 Palmitoleic is used in skin make-up to hide blemishes.
C16:1 Palmitoleic is also used in certain surfactants as a cleaning agent.
C16:1 Palmitoleic is the most common saturated fatty acid found in the human body and can be provided in the diet or synthesized endogenously from other fatty acids, carbohydrates and amino acids.
C16:1 Palmitoleic is a major component of palm oil (44% of total fats), but significant amounts of C16:1 Palmitoleic can also be found in meat and dairy products (50–60% of total fats), as well as cocoa butter (26%) and olive oil (8–20%).
Furthermore, C16:1 Palmitoleic is present in breast milk with 20–30% of total fats.
Effets of C16:1 Palmitoleic:
C16:1 Palmitoleic is used to produce soaps, cosmetics, and industrial mold release agents.
These applications use sodium palmitate, which is commonly obtained by saponification of palm oil.
C16:1 Palmitoleic strongly boosts metastasis in mouse models of human oral cancer cells.
Among all fatty acids, C16:1 Palmitoleic has the strongest effect in boosting the metastatic potential of CD36+ metastasis-initiating cells.
C16:1 Palmitoleic is a saturated fatty acid commonly found in both animals and plants.
C16:1 Palmitoleic is a major component in the oils from palm trees, such as palm oil, palm kernel oil and coconut oil.
C16:1 Palmitoleic, a kind of fatty acid, derived from palm oil.
C16:1 Palmitoleic is a saturated fatty acid that occurs in natural fats and oils, tall oil, and most commercial grade stearic acid.
C16:1 Palmitoleic is prepared by treating fats and oils with water at a high pressure and temperature, leading to the hydrolysis of triglycerides.
First-aid measures of C16:1 Palmitoleic
Eye Contact :
Rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes.
Getmedical attention.
Skin Contact :
Wash off immediately with plenty of water for at least 15 minutes.
Get medical attention.
Inhalation :
Remove from exposure, lie down.
Remove to fresh air.
Get medical attention.
If not breathing, give artificial respiration.
Ingestion :
Do NOT induce vomiting.
Get medical attention.
Substance identity
EC / List no.: 206-765-9
CAS no.: 373-49-9
Mol. formula: C16H30O2
Hazard classification & labelling of C16:1 Palmitoleic
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.
C16:1 Palmitoleic 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.
C16:1 Palmitoleic indicated, in 2009, as being intended to be registered by at least one company in the EEA.
C16:1 Palmitoleic 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.
C16:1 Palmitoleic listed in the EINECS, ELINCS, or NLP inventories.
Synonyms:
(Z)-hexadec-9-enoic acid
(Z)-hexadec-9-enoic acid
9-cis-Hexadecenoic acid
9-Hexadecenoic acid, (9Z)-
9-Hexadecenoic acid, (Z)-
Palmitoleic acid
palmitoleic acid
Palmitolinoleic acid
(9Z)-hexadec-9-enoic acid
(Z)-Hexadec-9-enoic acid
(Z)-hexadec-9-enoic acid
cis-9-Hexadecenoic Acid
hexadec-9-enoic acid
Undef-373-49-9
cis-9-Hexadecenoic acid
Cis-Palmitoleic acid
373-49-9
palmitoleic acid
373-49-9
(Z)-Hexadec-9-enoic acid
cis-9-Hexadecenoic acid
9-cis-Hexadecenoic acid
(Z)-9-hexadecenoic acid
zoomaric acid
Zoomeric acid
cis-Palmitoleic acid
Oleopalmitic acid
cis-9-palmitoleic acid
(9Z)-hexadec-9-enoic acid
(9Z)-Hexadecenoic acid
palmitoleate
Palmitolinoleic acid
9Z-hexadecenoic acid
9Z-palmitoleic acid
Hexadecenoate
Oleopalmitate
Zoomerate
cis-Palmitoleate
9-Hexadecenoate
9-cis-hexadecenoate
cis-delta-9-Hexadecenoic acid
cis-Delta(9)-hexadecenoic acid
(Z)-9-hexadecenoate
(Z)-Palmitoleic acid
9-Hexadecenoic acid, (9Z)-
16:1Delta9
cis-9-hexadecenoate
cis-delta-9-Hexadecenoate
(Z)-Hexadec-9-enoicacid
9-Hexadecenoic acid, (Z)-
(Z)-hexadec-9-enoate
209B6YPZ4I
CHEMBL453509
CHEBI:28716
C16:1n-7
FA 16:1
cis-.delta.9-Hexadecenoic acid
UNII-209B6YPZ4I
palmitoleic-acid
Physetoleic acid
NSC277452
NSC-277452
cis-Palmitoleicacid
EINECS 206-765-9
MFCD00004437
NSC 277452
AI3-36443
(Z)-9-hexadecenic acid
bmse000926
DSSTox_CID_21197
DSSTox_RID_79644
Hexadecenoate (n-C16:1)
DSSTox_GSID_41197
SCHEMBL33310
GTPL5547
DTXSID0041197
PALMITOLEIC ACID [WHO-DD]
ZINC8221009
Tox21_300950
BDBM50269531
LMFA01030056
Palmitoleic acid, analytical standard
AKOS015843187
CS-W012589
DB04257
FS-6301
HY-W011873
NCGC00248225-01
NCGC00248225-03
NCGC00254852-01
AC-33786
CAS-373-49-9
FA(16:1(9Z))
H0072
Palmitoleic acid, >=98.5% (GC), liquid
S3341
C08362
Q412366
16:1(N-7)
ED9A824A-5CB7-476E-884E-4216DD38386E
PALMITOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
PALMITOLEIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
PALMITOLEIC ACID (C16:1) (CONSTITUENT OF KRILL OIL) [DSC]
