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Palmitoleic acid is a monounsaturated omega-7 fatty acid with the chemical formula C16H30O2.
Palmitoleic acid a naturally occurring lipid commonly found in various animal and plant sources, including macadamia nuts, sea buckthorn, and fish oils.
Structurally, Palmitoleic acid consists of a 16-carbon chain with a single double bond at the seventh carbon from the methyl end (or ninth carbon from the carboxyl end), making it a cis-unsaturated fatty acid.
CAS Number: 373-49-9
EC Number: 206-765-9
Molecular Formula: C16H30O2
Molecular Weight: 254.41
Synonyms: palmitoleic acid, 373-49-9, (Z)-Hexadec-9-enoic acid, cis-9-Hexadecenoic acid, 9-cis-Hexadecenoic acid, zoomaric acid, Zoomeric acid, cis-9-palmitoleic acid, cis-Palmitoleic acid, Oleopalmitic acid, (Z)-9-hexadecenoic acid, (9Z)-hexadec-9-enoic acid, (9Z)-Hexadecenoic acid, 9Z-hexadecenoic acid, Palmitolinoleic acid, 9Z-palmitoleic acid, cis-delta-9-Hexadecenoic acid, Hexadecenoate, Oleopalmitate, Zoomerate, cis-Delta(9)-hexadecenoic acid, 16:1Delta9, cis-Palmitoleate, 9-Hexadecenoate, UNII-209B6YPZ4I, 9-Hexadecenoic acid, (Z)-, 209B6YPZ4I, (Z)-Palmitoleic acid, CHEBI:28716, 9-Hexadecenoic acid, (9Z)-, EINECS 206-765-9, 9-cis-hexadecenoate, cis-delta-9-Hexadecenoate, (Z)-Hexadec-9-enoicacid, NSC 277452, (Z)-9-hexadecenoate, AI3-36443, CHEMBL453509, DTXSID0041197, 9-HEXADECENOIC ACID, MFCD00004437, NSC-277452, FA 16:1, 16:1(N-7), Palmetoleic acid; Palmetoleic acid (C16:1 cis), cis-.delta.9-Hexadecenoic acid, Palmitoleicacid, palmitoleic-acid, Physetoleic acid, NSC277452, cis-Palmitoleicacid, C16:1n7, Z)-9-Hexadecen-1-ol; 9-cis-Hexadecenol; cis-9-Hexadecen-1-ol; cis-9-Hexadecenol; cis-?9-Hexadecenol, (Z)-9-hexadecenic acid, bmse000926, Fatty Acid 16:1 n-7, Hexadecenoate (n-C16:1), SCHEMBL33310, GTPL5547, DTXCID8021197, PALMITOLEIC ACID [WHO-DD], Tox21_300950, BDBM50269531, LMFA01030056, Palmitoleic acid, analytical standard, AKOS015843187, CS-W012589, DB04257, FS-6301, HY-W011873, NCGC00248225-01, NCGC00248225-03, NCGC00254852-01, AC-33786, BP-29012, CAS-373-49-9, FA(16:1(9Z)), DB-371670, H0072, NS00015112, Palmitoleic acid, >=98.5% (GC), liquid, C08362, D82037, PALMITOLEIC ACID (CONSTITUENT OF SPIRULINA), Q412366, BRD-K91356052-001-04-0, PALMITOLEIC ACID (CONSTITUENT OF SAW PALMETTO), ED9A824A-5CB7-476E-884E-4216DD38386E, PALMITOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC], PALMITOLEIC ACID (C16:1) (CONSTITUENT OF KRILL OIL), PALMITOLEIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Palmitoleic acid is a monounsaturated omega-7 fatty acid with the chemical formula C16H30O2.
Palmitoleic acid is a naturally occurring lipid commonly found in various animal and plant sources, including macadamia nuts, sea buckthorn, and fish oils.
Structurally, Palmitoleic acid consists of a 16-carbon chain with a single double bond at the seventh carbon from the methyl end (or ninth carbon from the carboxyl end), making it a cis-unsaturated fatty acid.
Palmitoleic acid is biosynthesized in the human body through the desaturation of palmitic acid by the enzyme stearoyl-CoA desaturase (SCD).
Known for its beneficial properties, Palmitoleic acid plays a significant role in metabolic health, demonstrating anti-inflammatory and insulin-sensitizing effects.
Palmitoleic acid is also recognized for its potential in promoting skin health, enhancing wound healing, and serving as an antimicrobial agent.
Additionally, Palmitoleic acid is being investigated for its applications in reducing cardiovascular risk and supporting liver function.
Due to its unique properties, palmitoleic acid is gaining attention as a nutraceutical and functional food ingredient.
Palmitoleic acid is a naturally occurring monounsaturated omega-7 fatty acid, identified by the chemical formula C16H30O2.
Palmitoleic acid consists of a 16-carbon chain with a single double bond located between the seventh and eighth carbons from the methyl end (ω-7 position), giving it a cis configuration.
Palmitoleic acid is a derivative of palmitic acid and is biosynthesized in the human body through the enzymatic activity of stearoyl-CoA desaturase (SCD), which introduces a double bond into the saturated palmitic acid molecule.
Palmitoleic acid is found in both animal and plant-based sources, with high concentrations present in macadamia nuts, sea buckthorn oil, certain fish oils, and adipose tissue.
Palmitoleic acid also occurs in trace amounts in human plasma as part of triglycerides, phospholipids, and free fatty acids.
Palmitoleic acid is notable for its broad spectrum of physiological and biochemical roles.
Palmitoleic acid has been extensively studied for its potential to modulate metabolic health, particularly in the context of insulin sensitivity and glucose metabolism.
Research indicates that Palmitoleic acid exerts anti-inflammatory effects and can reduce chronic low-grade inflammation, a common feature of metabolic disorders such as type 2 diabetes and obesity.
Additionally, palmitoleic acid has been associated with improved lipid profiles, including the reduction of low-density lipoprotein (LDL) cholesterol and triglycerides, and an increase in high-density lipoprotein (HDL) cholesterol, suggesting a protective role against cardiovascular disease.
Beyond its metabolic benefits, palmitoleic acid also plays a vital role in maintaining skin health.
Palmitoleic acid is a key component of sebum, the natural oil produced by sebaceous glands, which helps to moisturize the skin and protect it from environmental stressors.
Palmitoleic acid's antimicrobial properties further contribute to the skin’s defense mechanisms, making it a potential therapeutic agent for conditions such as acne, dermatitis, and wound healing.
Moreover, palmitoleic acid demonstrates hepatoprotective properties, aiding in the reduction of liver fat accumulation and supporting liver function.
The industrial and commercial applications of palmitoleic acid are expanding, particularly in the fields of nutraceuticals, functional foods, and cosmetics.
Palmitoleic acid is increasingly recognized as a beneficial dietary supplement due to its unique health-promoting properties.
Palmitoleic acid's ability to regulate inflammatory pathways, support metabolic and cardiovascular health, and enhance skin barrier function has made it a subject of growing interest among researchers and health professionals alike.
As more studies elucidate Palmitoleic acid's mechanisms of action and potential therapeutic uses, palmitoleic acid continues to gain prominence as a versatile and valuable bioactive compound.
Palmitoleic acid is an omega-7 monounsaturated fatty acid that is found in plants and marine sources.
Macadamia nuts and buckthorn seed oil contain the cis isomer of palmitoleic acid, and dairy products are rich sources of trans-palmitoleate.
Palmitoleic acid has been reported to have beneficial effects on insulin sensitivity, cholesterol metabolism, and hemostasis.
Palmitoleic acid has been proposed that palmitoleic acid may prevent beta-cell apoptosis induced by glucose or saturated fatty acids.
Palmitoleic acid is a long-chain monounsaturated fatty acid of 16 carbon atoms.
Structurally, Palmitoleic acid is an omega-7 fatty acid.
Palmitoleic acid is usually found at a trace level in commonly used vegetable oils.
Interestingly, pulp oil from berries of sea buckthorn contains palmitoleic acid at a remarkable level (32-42%).
Macadamia nut oil contains a high level of palmitoleic acid (17-19%) as well.
Other plant oils with a relatively high percentage of palmitoleic acid are milkweed oil and avocado oil.
The diatom Phaeodactylum tricornutum is an excellent source of palmitoleic acid as it contains very high levels of this fatty acid.
The palmitoleic acid content of seaweeds depends on the taxa, geographical location and sampling season and usually ranges from 0-9%.
Sugar kelp (Saccharina litissima) harvested in certain seasons contain a relatively good amount of palmitoleic acid.
Compared to oleaginous yeasts, non-oleaginous yeasts such as Saccharomyces cerevisiae and Kluyveromyces polysporine accumulate a high amount of palmitoleic acid.
Palmitoleic acid functions as a lipokine and is linked to lipid metabolism and insulin sensitivity.
Apart from this, Palmitoleic acid has an anti-inflammatory role as well.
Palmitoleic acid may be used as a feed supplement for dairy cows as palmitic acid supplementation improves milk quality and yield.
Fortification of eggs with palmitoleic acid is feasible with feeding the laying hens with fish oil rather than macroalgal oil.
Oils rich in palmitoleic acid can be excellent feedstocks for biodiesel production with the improved cold flow, a critical fuel property.
Palmitoleic acid, 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 that is a common constituent of the glycerides of human adipose tissue.
Present in all tissues, it is generally found in higher concentrations in the liver.
Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40% respectively.
Palmitoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Palmitoleic acid, commonly known as omega-7, is a rare monounsatured fatty acid, which was generally reported to benefit the skin in promoting epithelialisation, and certain gynaecological problems (vaginal mycoses).
Until now, sea buckthorn (Hippophae rhamnoides), a shrub widely found in Europe and Asia, and macadamia nuts have been the principal sources.
Palmitoleic acid (PMA) has anti-inflammatory and antidiabetic activities.
Palmitoleic acid is a gap junction uncoupler.
Palmitoleic acid, 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.
Palmitoleic acid is a rare component of fats.
Palmitoleic acid is a common constituent of the glycerides of human adipose tissue.
Palmitoleic acid is present in all tissues but, in general, found in higher concentrations in the liver.
Palmitoleic acid is biosynthesized from palmitic acid by the action of the enzyme Stearoyl-CoA desaturase-1.
Palmitoleic acid is a fatty acid that has been shown to have anti-inflammatory effects.
Palmitoleic acid inhibits the production of pro-inflammatory cytokines and attenuates the activation of macrophages, as well as inhibiting the expression of genes involved in cell proliferation.
Palmitoleic acid has also been shown to be effective against bowel disease, such as Crohn's disease.
In a low-dose group, palmitoleic acid inhibited the production of matrix metalloproteinases in 3T3-L1 preadipocytes and hl-60 cells.
Palmitoleic acid also decreased the release of basic proteins from these cells and increased their energy metabolism.
Uses of Palmitoleic Acid:
Palmitoleic acid has a wide range of applications in health, nutrition, skincare, and industry, owing to its unique chemical properties and physiological benefits.
In the field of health and wellness, Palmitoleic acid is commonly used as a dietary supplement to support metabolic and cardiovascular health, improve insulin sensitivity, and reduce inflammation, making it beneficial for conditions like type 2 diabetes, obesity, and heart disease.
Palmitoleic acid also plays a role in liver health by helping to prevent fat accumulation and improving overall function.
In skincare, palmitoleic acid is a natural component of sebum and is widely valued for its ability to hydrate the skin, repair the skin barrier, and combat microbial infections, making it a key ingredient in anti-aging, moisturizing, and acne treatment products.
Industrially, Palmitoleic acid is utilized in the production of functional foods, biofuels, and eco-friendly lubricants due to its chemical stability and renewable nature.
The versatility of palmitoleic acid continues to expand as research explores its potential in pharmaceuticals, veterinary care, and sustainable industrial applications.
Palmitoleic acid is a versatile bioactive compound with applications spanning across healthcare, nutrition, cosmetics, and industrial sectors.
Palmitoleic acid's unique chemical properties and physiological benefits make it valuable in several areas:
Nutritional and Health Applications:
Metabolic Health Support:
Palmitoleic acid is known to improve insulin sensitivity and regulate glucose metabolism, making it a promising supplement for managing type 2 diabetes and metabolic syndrome.
Palmitoleic acid also helps in reducing inflammation, which is a common factor in various chronic diseases.
Cardiovascular Health:
Palmitoleic acid may help lower harmful LDL cholesterol and triglycerides while raising beneficial HDL cholesterol, reducing the risk of atherosclerosis and cardiovascular diseases.
Weight Management:
Palmitoleic acid is believed to regulate lipid metabolism and reduce fat accumulation, potentially aiding in weight management and the prevention of obesity-related conditions.
Liver Health:
Palmitoleic acid has hepatoprotective properties, helping reduce fat buildup in the liver (non-alcoholic fatty liver disease) and improving overall liver function.
Cosmetic and Skin Care:
Moisturizer and Skin Barrier Support:
As a natural component of sebum, palmitoleic acid is a powerful emollient that helps maintain skin hydration and elasticity.
Palmitoleic acid supports the repair of the skin barrier, making it a popular ingredient in anti-aging and moisturizing products.
Wound Healing:
Palmitoleic acid's anti-inflammatory and antimicrobial properties make it effective in accelerating wound healing and treating minor skin irritations and infections.
Anti-Acne and Antimicrobial Agent:
Palmitoleic acid’s ability to combat microbial growth, including acne-causing bacteria, has led to its inclusion in formulations targeting acne-prone skin.
Industrial and Pharmaceutical Applications:
Nutraceuticals:
Due to Palmitoleic acid's health benefits, palmitoleic acid is increasingly used in dietary supplements, often marketed for its cardiovascular, anti-inflammatory, and metabolic advantages.
Functional Foods:
Palmitoleic acid is incorporated into food products designed to promote health beyond basic nutrition, such as omega-enriched oils and beverages.
Cosmetics Industry:
As a bio-based ingredient, Palmitoleic acid is widely utilized in creams, serums, and lotions for its moisturizing and anti-aging properties.
Pharmaceuticals:
Research is ongoing into Palmitoleic acid's potential therapeutic uses for treating conditions like inflammatory disorders, metabolic syndromes, and skin diseases.
Emerging Applications:
Biofuels and Lubricants:
The chemical stability and low oxidation rate of palmitoleic acid make it suitable for use in the production of bio-based lubricants and fuels, offering a sustainable alternative to petrochemicals.
Animal Health:
Palmitoleic acid is being explored as a dietary supplement in veterinary care to enhance skin and coat health and support overall metabolism in pets and livestock.
Industry Uses of Palmitoleic acid:
Finishing agents
Agricultural chemicals (non-pesticidal)
Lubricating agent
Surface active agents
Lubricants and lubricant additives
Adhesives and sealant chemicals
Intermediate
Fuel
Dietary sources of Palmitoleic acid:
Palmitoleic acid 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 palmitoleic acid 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.
Palmitoleic acid is a kind of fatty acid in human milk.
Among SHRSP given various fatty acids, a diet containing 1% Palmitoleic acid significantly improves the survival rate, with concomitant reduction in the incidence of stroke in spite of their excess NaCl intake through 1% NaCl water for drinking.
Health Benefits of Palmitoleic Acid:
Improves Insulin Sensitivity:
Palmitoleic acid may enhance insulin sensitivity in liver and skeletal muscles, and it could help reduce the risk of diabetes.
Anti-Inflammatory Effects:
Palmitoleic acid has been shown to suppress inflammatory markers in adipose tissue.
Cardiovascular Health Benefits:
Palmitoleic acid potentially decreases serum triglyceride and cholesterol levels, and may normalize levels of HDL and LDL-cholesterol in individuals with hypercholesterolemia.
Supplementation with macadamia oil, which has a high proportion of palmitoleic acid, promotes a decrease in serum triglyceride and cholesterol levels.
Metabolic Health:
Due to Palmitoleic acid's beneficial effects on glucose and lipid metabolism, palmitoleic acid could help prevent or ameliorate metabolic syndrome.
Palmitoleic acid has demonstrated the ability to increase white adipocytes GLUT4 content and glucose uptake.
Immune System Modulation:
Palmitoleic acid exerts a suppressive effect on the immune system by reducing lymphocyte proliferation and decreasing the production of inflammatory cytokines.
Palmitoleic acid's effect is characterized by reduced Th1 and Th17 responses and modulation of co-stimulatory and apoptotic molecules.
Palmitoleic acid has potential as an anti-inflammatory agent in immune-related disorders.
PPAR Activation:
Palmitoleic acid demonstrates an ability to activate PPARα and PPARγ which provide multiple benefits for cardiometabolic health and weight management.
Activation of PPARα and PPARγ offers a wide range of benefits including improved lipid metabolism, enhanced insulin sensitivity, anti-inflammatory effects, better cardiovascular health, and efficient energy homeostasis.
These benefits make PPAR activation a promising therapeutic target for managing metabolic diseases, cardiovascular conditions, obesity, and inflammation-related disorders.
Skin Health:
Palmitoleic acid improves skin hydration and barrier function but shows less significant effects on elasticity and wrinkle reduction.
Biochemistry of Palmitoleic Acid:
Endogenous Synthesis:
Palmitoleic acid is primarily produced through de novo lipogenesis in the liver and adipose tissue via the enzyme Stearoyl-CoA desaturase 1 (SCD1) from palmitic acid.
Biosynthesis regulation is influenced by factors such as diet, hormones, and overall metabolic state.
Isomers:
The cis isoform (cis-palmitoleate) is produced endogenously, while the trans isoform can be generated from dietary vaccenic acid.
Role in Triglycerides:
After synthesis, palmitoleic acid is incorporated into triglycerides, phospholipids, waxes, and cholesterol esters.
Palmitoleic acid's a common constituent of human adipose tissue glycerides.
Beta Oxidation:
Palmitoleic acid is rapidly oxidized compared to other fatty acids.
Through beta oxidation, Palmitoleic acid can serve as an energy source for cells.
Metabolism Regulation:
Studies suggest palmitoleic acid may provide multiple metabolic benefits including improving insulin sensitivity in liver and skeletal muscles; PPAR-alpha activation; and increased lipid metabolism.
General Manufacturing Information of Palmitoleic Acid:
Palmitoleic acid is manufactured through various processes, depending on its source and intended use.
Palmitoleic acid can be extracted from natural sources such as macadamia nuts, sea buckthorn, and certain fish oils, using cold-pressing or solvent extraction methods.
For industrial-scale production, chemical synthesis or enzymatic processes are employed, often involving the desaturation of palmitic acid using stearoyl-CoA desaturase (SCD) enzymes.
Biotechnological advancements, such as microbial fermentation, are also being explored to produce palmitoleic acid in a more sustainable and cost-effective manner.
Once extracted or synthesized, the fatty acid is refined and purified for use in applications like dietary supplements, cosmetics, functional foods, and industrial products such as bio-based lubricants and eco-friendly materials.
The growing demand for omega-7 fatty acids in nutraceuticals and personal care products has driven innovation in Palmitoleic acid's manufacturing processes to ensure high purity and scalability.
Industry Processing Sectors:
Paper Manufacturing
Plastics Product Manufacturing
Miscellaneous Manufacturing
Food, beverage, and tobacco product manufacturing
Other (requires additional information)
All Other Basic Organic Chemical Manufacturing
Agricultural chemicals (non-pesticidal)
Not Known or Reasonably Ascertainable
Adhesives and sealant chemicals
Handling and Storage of Palmitoleic Acid:
Handling:
Handle palmitoleic acid with care to avoid spills or contact with skin and eyes.
Use appropriate personal protective equipment (PPE), such as gloves and goggles, in well-ventilated areas.
Avoid inhalation of vapors or mists.
Do not eat, drink, or smoke while handling the material.
Storage:
Store in a cool, dry, and well-ventilated area, away from heat, open flames, and direct sunlight.
Use tightly sealed containers made of compatible materials, such as stainless steel or glass, to prevent oxidation.
Keep away from strong oxidizers, acids, and bases.
Properly label containers to prevent accidental misuse.
Stability and Reactivity of Palmitoleic Acid:
Stability:
Palmitoleic acid is generally stable under normal conditions but can oxidize when exposed to air, light, or heat, leading to rancidity.
Reactivity:
Palmitoleic acid reacts with strong oxidizing agents and may degrade into harmful by-products under extreme conditions, such as high temperatures or prolonged exposure to ultraviolet light.
Decomposition Products:
Thermal decomposition can produce carbon monoxide, carbon dioxide, and other toxic fumes.
Incompatibilities:
Avoid contact with strong acids, bases, and oxidizers to prevent hazardous reactions.
First Aid Measures of Palmitoleic Acid:
Eye Contact:
Rinse thoroughly with plenty of water for at least 15 minutes.
Remove contact lenses if present and easy to do.
Seek medical attention if irritation persists.
Skin Contact:
Wash the affected area with soap and water.
Remove contaminated clothing.
Seek medical advice if irritation or an allergic reaction occurs.
Inhalation:
Move the individual to fresh air.
If breathing is difficult, provide oxygen and seek medical attention immediately.
Ingestion:
Do not induce vomiting. Rinse mouth thoroughly with water.
Seek medical advice if symptoms occur or if a large quantity is ingested.
Firefighting Measures of Palmitoleic Acid:
Extinguishing Media:
Use foam, carbon dioxide (CO₂), dry chemical, or water spray to extinguish fires involving palmitoleic acid.
Specific Hazards:
Combustion of palmitoleic acid can produce toxic fumes, including carbon monoxide (CO) and carbon dioxide (CO₂).
Protective Equipment:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear to prevent exposure to smoke and fumes.
Additional Notes:
Prevent contaminated water from firefighting efforts from entering drains or waterways.
Accidental Release Measures of Palmitoleic Acid:
Personal Precautions:
Use PPE, including gloves, goggles, and respiratory protection, to avoid skin or eye contact and inhalation.
Ensure adequate ventilation in the spill area.
Environmental Precautions:
Avoid releasing into drains, soil, or waterways. Contain the spill to prevent environmental contamination.
Cleanup Methods:
Absorb the spill with inert materials such as sand, earth, or vermiculite, and place in a suitable container for disposal.
Clean the area with water and detergent after removing the bulk of the material.
Dispose of waste according to local regulations.
Exposure Controls / Personal Protective Measures of Palmitoleic Acid:
Engineering Controls:
Ensure adequate ventilation or use local exhaust systems to minimize exposure to vapors or aerosols.
Personal Protective Equipment (PPE):
Eye Protection:
Use safety goggles or face shields.
Skin Protection:
Wear chemical-resistant gloves and clothing.
Respiratory Protection:
Use a suitable respirator if exposure limits are exceeded or if ventilation is inadequate.
Hygiene Measures:
Wash hands thoroughly after handling.
Remove contaminated clothing and wash before reuse.
Avoid eating, drinking, or smoking in the work area.
Exposure Limits:
No specific occupational exposure limits are established, but general good practice should be followed to minimize exposure.
Identifiers of Palmitoleic Acid:
CAS Number: 373-49-9
ChEBI: CHEBI:28716
ChemSpider: 393216
ECHA InfoCard: 100.006.151
IUPHAR/BPS: 5547
PubChem CID: 445638
UNII: 209B6YPZ4I
CompTox Dashboard (EPA): DTXSID0041197
InChI: 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-
Key: SECPZKHBENQXJG-FPLPWBNLSA-N
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-
Key: SECPZKHBENQXJG-FPLPWBNLBE
SMILES: O=C(O)CCCCCCCC=C/CCCCCC
IUPAC Name: (9Z)-hexadec-9-enoic acid
Traditional IUPAC Name: palmitoleic acid
Formula: C16H30O2
InChI: 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-
InChI Key: SECPZKHBENQXJG-FPLPWBNLSA-N
Molecular weight: 254.4082
Exact mass: 254.224580204
SMILES: CCCCCCC=C/CCCCCCCC(O)=O
Linear Formula: CH3(CH2)5CH=CH(CH2)7COOH
CAS Number: 373-49-9
Molecular Weight: 254.41
Beilstein: 1725389
EC Number: 206-765-9
MDL number: MFCD00004437
UNSPSC Code: 12352211
PubChem Substance ID: 24899035
NACRES: NA.25
Chemical Formula: C16H30O2
Average Molecular Weight: 254.4082
Monoisotopic Molecular Weight: 254.224580204
IUPAC Name: (9Z)-hexadec-9-enoic acid
Traditional Name: palmitoleic acid
CAS Registry Number: 373-49-9
SMILES: CCCCCCC=C/CCCCCCCC(O)=O
InChI Identifier:
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-
InChI KeyfSECPZKHBENQXJG-FPLPWBNLSA-N
Properties of Palmitoleic Acid:
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)
Boiling Point: 146 °C @ Press: 0.4 Torr
Melting Point: -0.1 °C
Density: 0.8538 g/cm³ (liquid) @ Temp: 15 °C
Formal Name: (9Z)-hexadecenoic acid
CAS Number: 373-49-9
Molecular Formula: C16H30O2
Formula Weight: 254.4
Purity: ≥99%
Formulation: (Request formulation change) A neat oil
SMILES: CCCCCC/C=CCCCCCCCC(=O)O
InChi Key: SECPZKHBENQXJG-FPLPWBNLSA-N
Side Chain Carbon Sum: 16:1
Molecular Weight: 254.41 g/mol
XLogP3: 6.4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 13
Exact Mass: 254.224580195 Da
Monoisotopic Mass: 254.224580195 Da
Topological Polar Surface Area: 37.3Ų
Heavy Atom Count: 18
Complexity: 209
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
biological source: Macadamia integrifolia
Assay: ≥98.5% (GC)
form: liquid
refractive index: n20/D 1.457 (lit.)
bp: 162 °C/0.6 mmHg (lit.)
mp: 0.5 °C (lit.)
density: 0.895 g/mL at 20 °C (lit.)
Alternative Parents of Palmitoleic Acid:
Unsaturated fatty acids
Straight chain fatty acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Names of Palmitoleic Acid:
Preferred IUPAC name:
(9Z)-Hexadec-9-enoic acid
Other names:
Palmitoleic acid
cis-Palmitoleic acid
9-cis-Hexadecenoic acid
C16:1 (Lipid numbers)
9-Hexadecenoic acid, (9Z)-
9-Hexadecenoic acid, (Z)-
Palmitoleic acid
(9Z)-9-Hexadecenoic acid
cis-Δ9-Hexadecenoic acid
cis-9-Hexadecenoic acid
9-cis-Hexadecenoic acid
(Z)-9-Hexadecenoic acid
Zoomeric acid
cis-Palmitoleic acid
C16:1
Oleopalmitic acid
9Z-Hexadecenoic acid
9-Hexadecenoic acid
(Z)-Hexadec-9-enoic acid
