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C16:1 Palmitoleic is used in organic synthesis, and as a standard in chromatographic analysis.
C16:1 Palmitoleic is used in cosmetic and personal care formulations as an emollient that helps improve skin softness and smoothness.
C16:1 Palmitoleic is applied in skincare products to support the skin barrier and provide moisturizing and conditioning effects.
CAS Number: 373-49-9
Molecular Formula:C16H30O2
Molecular Weight:254.41 g·mol−1
SYNONYMS:
(9Z)-Hexadec-9-enoic acid, Palmitoleic acid, cis-Palmitoleic acid, 9-cis-Hexadecenoic acid, C16:1 (Lipid numbers), 9-HEXADECENOIC ACID,C16:1,Zoomaric acid,CIS-9-HEXADECENOIC ACID,PALM ACID,(Z)-9-hexadecenoic acid,cis-Palmitoleic acid,Palmitoleic Acid(PA),(Z)-hexadec-9-enoic acid,(E)-hexadec-9-enoic acid, 9-Hexadecenoic acid, (Z)-, Palmitoleic acid, (Z)-9-Hexadecenoic acid, (Z)-Hexadec-9-enoic acid, 9-Hexadecenoic acid, 9-cis-Hexadecenoic acid, 9Z-Hexadecenoic acid, C16:1, Oleopalmitic acid, Zoomeric acid, cis-9-Hexadecenoic acid, cis-Palmitoleic acid, cis--delta-9-Hexadecenoic acid, cis-9-Hexadecenoic acid, cis-9-Hexadecenoic acid, 9-Hexadecenoic acid, (Z)-, cis-δ9-Hexadecenoic acid, Palmitolinoleic acid, 9-cis-Hexadecenoic acid, (Z)-9-Hexadecenoic acid, (E)-9-Hexadecenoic acid, (Z)-Palmitoleic acid, cis-Hexadec-9-enoic acid, cis-Palmitoleic acid, trans-9-Hexadecenoic acid, (Z)-hexadec-9-enoic acid, Palmitoleic acid, cis-Palmitoleic acid, (Z)-hexadec-9-enoic acid, 9-cis-hexadecenoic acid, C16:1 (CIS-9) acid, (9Z)-hexadec-9-enoic acid, Zoomaric acid, Oleopalmitic acid, C16:1n-7, 9Z-Hexadecenoic acid, Palmetoleic acid
C16:1 Palmitoleic, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH.
C16:1 Palmitoleic is a rare component of fats.
C16:1 Palmitoleic 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.
C16:1 Palmitoleic is a hexadecenoic acid with a cis-double bond at position C-9.
C16:1 Palmitoleic is a monounsaturated fatty acid found in macadamia oil and also in blood plasma.
In the human body, C16:1 Palmitoleic is produced via endogenous fat synthesis.
C16:1 Palmitoleic, is a monounsaturated fatty acid with 16 carbon atoms in the fatty acid chain.
This fatty acid, C16:1 Palmitoleic is characterized by having one double bond between the 9th and 10th carbon atoms, counted from the methyl end.
Another monounsaturated fatty acid is C18:1 sum.
C16:1 Palmitoleic is naturally found in foods such as fish, nuts, seeds, and meat.
C16:1 Palmitoleic, or (9X)-hexadec-9-enoic acid, is a 13C labeled omega-7 monounsaturated fatty acid.
C16:1 Palmitoleic is a common component of glycerides in human adipose tissue and is studied in metabolic research for its role in liver metabolism.
C16:1 Palmitoleic is a monounsaturated fatty acid with a 16-carbon chain and a single cis double bond at the 9th carbon (from the carboxyl end).
C16:1 Palmitoleic is an omega-7 fatty acid biosynthesized in the body from palmitic acid by the enzyme stearoyl-CoA desaturase-1.
C16:1 Palmitoleic is found naturally in animal fats, plant oils (notably macadamia and sea buckthorn), and human tissues such as adipose and liver.
C16:1 Palmitoleic participates in lipid metabolism and has been studied for potential biological effects including insulin sensitivity and anti-inflammatory activity.
C16:1 Palmitoleic, or (Z)-9-hexadecenoic acid, is an omega-7 monounsaturated fatty acid 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 generally found in higher concentrations in the liver.
C16:1 Palmitoleic is biosynthesized from palmitic acid by the action of the enzyme delta-9 desaturase.
A beneficial fatty acid, C16:1 Palmitoleic has been shown to increase insulin sensitivity by suppressing inflammation, as well as inhibit the destruction of insulin-secreting pancreatic beta cells.
C16:1 Palmitoleic is a clear liquid.
C16:1 Palmitoleic is a monounsaturated fatty acid containing a 16-carbon chain with one double bond, commonly identified as C16:1.
C16:1 Palmitoleic occurs naturally in various plant and animal sources, including macadamia oil, sea buckthorn oil, and certain fish oils.
C16:1 Palmitoleic belongs to the omega-7 fatty acid family and is recognized for its unique biochemical and functional properties.
At room temperature, C16:1 Palmitoleic appears as an oily liquid with typical fatty acid characteristics such as hydrophobicity and lubricity.
This fatty acid, C16:1 Palmitoleic, is valued as a specialty ingredient due to its relatively limited natural availability compared to more common fatty acids.
C16:1 Palmitoleic plays an important role in cosmetic, nutritional, and industrial applications where monounsaturated fatty acids are required.
USES and APPLICATIONS of C16:1 PALMITOLEIC:
C16:1 Palmitoleic is used in cosmetic and personal care formulations as an emollient that helps improve skin softness and smoothness.
C16:1 Palmitoleic is applied in skincare products to support the skin barrier and provide moisturizing and conditioning effects.
C16:1 Palmitoleic is commonly used in hair care formulations, where it enhances shine, manageability, and conditioning performance.
In the nutraceutical and dietary supplement industries, C16:1 Palmitoleic is valued for its role in metabolic and cardiovascular health support.
C16:1 Palmitoleic is used in pharmaceutical research for studying lipid metabolism and anti-inflammatory activity.
C16:1 Palmitoleic serves as a raw material in the synthesis of specialty esters and surfactants for industrial applications.
C16:1 Palmitoleic is applied in the production of bio-based lubricants and metalworking fluids due to its natural lubricity.
In soap and cleansing product formulations, C16:1 Palmitoleic contributes to mildness and creamy foam characteristics.
C16:1 Palmitoleic is also used in research and development as a reference fatty acid for biochemical and nutritional studies.
From an industrial and formulation standpoint, C16:1 Palmitoleic is valued for its emollient characteristics and compatibility with skin lipids.
In cosmetic and personal care applications, C16:1 Palmitoleic is sometimes described as a “skin-identical” or “biomimetic” fatty acid because it resembles lipids naturally present in human sebum.
This similarity contributes to good skin feel, spreadability, and barrier-supporting properties when C16:1 Palmitoleic is used in creams, serums, and oil blends.
Unlike polyunsaturated fatty acids, C16:1 Palmitoleic exhibits moderate oxidative stability, making it less prone to rapid rancidification while still providing desirable sensory attributes.
In food and nutritional contexts, C16:1 Palmitoleic occurs naturally in certain oils such as macadamia oil and sea buckthorn oil, as well as in smaller amounts in dairy fat, fish oils, and meat.
C16:1 Palmitoleic's concentration in these sources is influenced by species, diet, and processing conditions.
Although it has been marketed in some supplements for potential metabolic or anti-inflammatory benefits, regulatory authorities generally regard such claims as investigational rather than established, emphasizing that C16:1 Palmitoleic is a normal dietary and endogenous lipid rather than a pharmacologically active substance.
Chemically, C16:1 Palmitoleic behaves as a weak organic acid due to its terminal carboxyl group.
C16:1 Palmitoleic readily forms salts (palmitoleates) with alkali metals and can undergo esterification to produce fatty acid esters used in flavors, fragrances, cosmetics, and specialty lubricants.
Like other unsaturated fatty acids, C16:1 Palmitoleic is susceptible to oxidation at the double bond when exposed to heat, light, or oxygen, which is why antioxidants or inert atmospheres are commonly used during storage and formulation.
In laboratory and analytical chemistry, C16:1 Palmitoleic is frequently used as a reference compound in lipid profiling, gas chromatography (GC), and mass spectrometry (MS) analyses.
C16:1 Palmitoleic is often derivatized to fatty acid methyl esters (FAMEs) to improve volatility and chromatographic performance.
C16:1 Palmitoleic's retention behavior and mass spectral pattern make it useful for distinguishing monounsaturated C16 fatty acids from their saturated or trans-isomer counterparts.
C16:1 Palmitoleic occupies an intermediate position between saturated and polyunsaturated fatty acids in terms of physical behavior, stability, and biological function.
This balance explains its relevance across nutrition science, biochemistry, cosmetics, and analytical chemistry, even though C16:1 Palmitoleic is less widely discussed than more abundant fatty acids such as palmitic or oleic acid.
Food & Nutritional Context: C16:1 Palmitoleic is found in dietary fats and oils and studied for potential metabolic benefits (e.g., improving insulin sensitivity, modulating inflammation in preclinical studies).
Cosmetic / Personal Care Uses of C16:1 Palmitoleic: Utilized for its emollient and moisturizing properties in some formulations (not a widespread common ingredient but present in specialty products).
C16:1 Palmitoleic is used in organic synthesis, and as a standard in chromatographic analysis.
C16:1 Palmitoleic is a polyunsaturated fatty acid which contributes to reduced protein oxidation in mammals.
-Industrial & Research Uses of C16:1 Palmitoleic:
Analytical Reference Standard:
C16:1 Palmitoleic is used as a standard in chromatographic and lipid analyses.
Organic Synthesis:
C16:1 Palmitoleic is used Intermediate or building block in research and specialty chemical synthesis.
FUNCTIONAL CHARACTERISTICS & BENEFITS of C16:1 PALMITOLEIC:
C16:1 Palmitoleic is an omega-7 monounsaturated fatty acid that plays a role in lipid metabolism and has been linked in research to anti-inflammatory effects and metabolic regulation, though further human studies are needed for definitive health claims.
C16:1 Palmitoleic contributes to membrane fluidity due to its unsaturation.
C16:1 Palmitoleic is a naturally occurring monounsaturated fatty acid characterized by a 16-carbon backbone with a single cis double bond, typically located at the Δ9 position.
This cis configuration introduces a structural “kink” into the hydrocarbon chain, reducing intermolecular packing efficiency and resulting in a lower melting point compared with its saturated analogue, palmitic acid.
This structural feature is responsible for C16:1 Palmitoleic remaining liquid or semi-liquid at room temperature and contributes to its functional behavior in biological membranes and lipid formulations.
From a biochemical perspective, C16:1 Palmitoleic is classified as an omega-7 fatty acid and is synthesized endogenously in mammals via the enzymatic desaturation of palmitic acid by stearoyl-CoA desaturase-1 (SCD-1).
Because C16:1 Palmitoleic is produced internally rather than being strictly essential in the diet, it is considered a non-essential fatty acid.
Nevertheless, circulating levels of C16:1 Palmitoleic have been investigated as biomarkers of de novo lipogenesis and metabolic status, particularly in studies related to insulin sensitivity, lipid metabolism, and hepatic fat accumulation.
In biological systems, C16:1 Palmitoleic is incorporated into triglycerides, phospholipids, and cholesteryl esters.
C16:1 Palmitoleic's presence in phospholipid bilayers influences membrane fluidity, permeability, and lipid signaling pathways.
Compared with longer or more highly unsaturated fatty acids, C16:1 Palmitoleic provides a balance between oxidative stability and membrane flexibility.
This makes C16:1 Palmitoleic relevant in tissues with active lipid turnover, such as the liver, adipose tissue, and skin.
OCCURRENCE & NATURAL SOURCES of C16:1 PALMITOLEIC:
C16:1 Palmitoleic occurs in small amounts in most dietary fats but is especially present in:
*Macadamia oil (~17%)
*Sea buckthorn oil (~19–29%)
*Fish and marine oils
*Human adipose tissue and liver triglycerides
C16:1 Palmitoleic is an endogenous fatty acid produced in mammals by desaturation of palmitic acid.
BIOCHEM/PHYSIOL ACTIONS of C16:1 PALMITOLEIC:
C16:1 Palmitoleic is a 16-carbon, omega-7, monounsaturated fatty acid that is enriched in the triglycerides of human adipose tissue and in liver.
OCCURRENCE of C16:1 PALMITOLEIC:
C16:1 Palmitoleic can be abbreviated as 16:1Δ9.
Dietary sources of C16:1 Palmitoleic include a variety of animal oils, vegetable oils, and marine oils.
Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources with high concentrations, containing 17% and 40% of C16:1 Palmitoleic, respectively.
CHEMICAL PROPERTIES of C16:1 PALMITOLEIC:
C16:1 Palmitoleic, also called cis-9-hexadecenoic acid, formula CH3(CH2)5CH=CH(CH2)7COOH.
C16:1 Palmitoleic is an unsaturated fatty acid found in nearly every fat, especially in marine oils (15–20%).
At room temperature, C16:1 Palmitoleic is a colorless liquid.
C16:1 Palmitoleic is insoluble in water; soluble in alcohol and ether.
NATURAL SOURCES of C16:1 PALMITOLEIC:
C16:1 Palmitoleic is found in trace amounts in most foods except for sardine oil, which contains 15% of this acid as a component of triglycerides.
Other 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% C16:1 Palmitoleic, respectively.
Mink oil is also a source of C16:1 Palmitoleic.
PHYSICAL and CHEMICAL PROPERTIES of C16:1 PALMITOLEIC:
Chemical formula:C16H30O2
Molar mass:254.414 g·mol−1
Density:0.894 g/cm3
Melting point:−0.1 °C (31.8 °F; 273.0 K)
CBNumber:CB1384985
Molecular Formula:C16H30O2
Molecular Weight:254.41
MDL Number:MFCD00004437
MOL File:373-49-9.mol
Melting point:0.5 °C (lit.)
Boiling point:162 °C/0.6 mmHg (lit.)
Density:0.895 g/mL at 20 °C (lit.)
refractive index:1.457-1.459
Flash point:62 °C
storage temp.:-20°C
solubility:Chloroform,Methanol (Slightly)
form:Liquid
pka:4.78±0.10(Predicted)
color:Clear
biological source:Macadamia integrifolia
BRN:1725389
Cosmetic Ingredient Review (CIR):PALMITOLEIC ACID (373-49-9)
InChI:1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-
InChIKey:SECPZKHBENQXJG-FPLPWBNLSA-N
SMILES:CCCCCCC=C/CCCCCCCC(O)=O
LogP:6.402 (est)
CAS DataBase Reference:373-49-9
FDA 21 CFR:357.210
EWG's Food Scores:1
FDA UNII:209B6YPZ4I
EPA Substance Registry System:9-Hexadecenoic acid, (9Z)- (373-49-9)
UNSPSC Code:85151701
NACRES:NA.25
Formula:C16 H30 O2
Mass:254.41
IUPAC name:(Z)-hexadec-9-enoic acid
inchi:InChI=1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-/f/h17H
stdinchi:InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-
stdinchikey:SECPZKHBENQXJG-FPLPWBNLSA-N
smiles:C(CCCCCCCC=C/CCCCCC)(=O)O
Linear Formula:CH3(CH2)5CH=CH(CH2)7COOH
CAS Number:373-49-9
Molecular Weight:254.41
UNSPSC Code:85151701
NACRES:NA.24
PubChem Substance ID:329766568
EC Number:206-765-9
Beilstein/REAXYS Number:1725389
MDL number:MFCD00004437
Physical state:liquid
Color:colourless
Odor:No data available
Melting point/freezing point:Melting point/range:0.5 °C - lit.
Initial boiling point and boiling range:162 °C at 0.8 hPa - lit.
Flammability (solid,gas):No data available
Upper/lower flammability or explosive limits:No data available
Flash point:62 °C - closed cup
Autoignition temperature:No data available
Decomposition temperature:No data available
pH:No data available
Viscosity:Viscosity, kinematic:No data available
Viscosity, dynamic:No data available
Water solubility:practically insoluble
Partition coefficient:n-octanol/water log Pow:ca.6.4 - (Lit.),Potential bioaccumulation
Vapor pressure:No data available
Density:0.895 g/mL at 20 °C - lit.
Relative density:No data available
Relative vapour density:No data available
Particle characteristics:No data available
Explosive properties:No data available
Oxidizing properties:none
Other safety information:No data available
CAS Number:373-49-9
Molecular Formula:C16H30O2
Molecular Weight:254.414 g/mol
Beilstein Registry Number:1725389
EC Number:206-765-9
MDL Number:MFCD00004437
IUPAC Name:(9Z)-hexadec-9-enoic acid
Common Name:Palmitoleic acid
CAS Number:373-49-9
EC / EINECS Number:206-765-9
Molecular Formula:C₁₆H₃₀O₂
Molecular Weight:~254.41 g/mol
PubChem CID:445638
ChemSpider ID:393216
SMILES:O=C(O)CCCCCCCC=C/CCCCCC
InChIKey:SECPZKHBENQXJG-FPLPWBNLSA-N
Physical State & Appearance
Physical Form:Clear,colorless to pale yellow liquid at room temperature
Odor:Fatty/oily (typical of long-chain fatty acids)
Key Properties
Melting Point:~0.5 °C (some sources report ~-0.1 °C)
Boiling Point:~162 °C (at ~0.6 mmHg)
Density:~0.894–0.895 g/mL at ~20 °C
Refractive Index:~1.457–1.459
Flash Point:~62 °C
Solubility:
Water:Practically insoluble
Soluble (slightly):Organic solvents such as methanol or chloroform
Predicted pKa:~4.78 (carboxyl group acidity)
LogP:~6.4–6.6 (lipophilicity estimate)
Vapor Pressure:Very low at ambient temperature
FIRST AID MEASURES of C16:1 PALMITOLEIC:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of C16:1 PALMITOLEIC:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of C16:1 PALMITOLEIC:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of C16:1 PALMITOLEIC:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of C16:1 PALMITOLEIC:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of C16:1 PALMITOLEIC:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
