PRODUCTS

C14:1 MYRISTOLEIC ACID

C14:1 Myristoleic Acid is applied in cosmetic and personal care formulations as an emollient component that helps improve skin softness and smoothness.
C14:1 Myristoleic Acid is used in skincare products due to its lubricating properties and its ability to enhance spreadability.
C14:1 Myristoleic Acid is used as a raw material in the production of soaps and cleansing products, contributing to mildness and foam characteristics.

CAS Number: 544-64-9
EC / EINECS Number: 208-876-8
IUPAC Name: (9Z)-tetradec-9-enoic acid
Molecular Formula: C₁₄H₂₆O₂
Molecular Weight: 226.35 g/mol

SYNONYMS:
Myristoleic acid, (9Z)-tetradec-9-enoic acid, 9-tetradecenoic acid, cis-9-tetradecenoic acid, cis-Δ9-tetradecenoic acid, (Z)-9-Tetradecenoic acid, Myristolenic acid, Oleomyristic acid, C14:1 (CIS-9) acid, 9Z-tetradecenoic acid, FA 14:1, Omega-5 fatty acid, Myristoleic acid, 544-64-9, (Z)-Tetradec-9-enoic acid, 9Z-tetradecenoic acid, cis-9-tetradecenoic acid, 9-Tetradecenoic acid, (9Z)-, 9-Tetradecenoic acid, (9Z)-Tetradecenoic acid, RF23WGD123, cis-tetradec-9-enoic acid, DTXSID5041568, CHEBI:27781, 14:1(N-5), RefChem:160412, Fatty Acid 14:1 n-5, DTXCID3021568, 208-876-8, (9Z)-tetradec-9-enoic acid, (z)-9-tetradecenoic acid, 9-cis-Tetradecenoic acid, 9-Tetradecenoic acid, (Z)-, cis-Delta(9)-tetradecenoic acid, CHEMBL456732, MFCD00004436, FA 14:1, Myristolenic acid, (9Z)-tetradecenoate, Oleomyristic acid, (Z)-9-Tetradecenoicacid, (9Z)-9-Tetradecenoic acid, miristoleic acid, EINECS 208-876-8, Z-9-Tetradecenoic acid, Myristoleic acid, 99%, Z-tetradec-9-enoic acid, Tetradecenoic acid (cis-9), UNII-RF23WGD123, SCHEMBL109270, orb1303126, orb3025302, SCHEMBL4350671, MSK1727, AAA54464, BDBM50269530, LMFA01030051, Myristoleic acid, analytical standard, AKOS037645073, EBC-615400, CIS-.DELTA.9-TETRADECENOIC ACID, AS-56816, BP-40619, DA-55798, FA(14:1(9Z)), Myristoleic acid, >=99% (capillary GC), HY-113332, CS-0059626, NS00020426, C08322, G12044, Q58221, (9Z)-Tetradec-9-enoic acid, 9-Tetradecenoic acid, 9-cis-Tetradecenoic acid, cis-Δ9-Tetradecenoic acid, Myristolenic acid, Oleomyristic acid, 9-tetradecenoic acid, CIS-9-TETRADECENOIC ACID, MYRISTOLEIC ACID, Myristolenic acid, C14:1 (CIS-9) ACID, MYRISTOLEIC ACID 99%, (z)-9-tetradecenoicaci, (Z)-9-Tetradecenoicacid, Myristoleic Acid(C14:1), 9(Z)-Tetradecanoic acid, cis-9-Tetradecenoic acid, myristoleic acid, (9Z)- tetradec-9-enoic acid, (Z)- tetradec-9-enoic acid, cis- tetradec-9-enoic acid, (9Z)- tetradecenoic acid, (9Z)-9- tetradecenoic acid, cis-9- tetradecenoic acid, 9- tetradecenoic acid, (9Z)-, 9- tetradecenoic acid, (Z)-, 9-Tetradecenoic acid, (9Z)- (9CI, ACI), (9Z)-9-Tetradecenoic acid (ACI), 9-Tetradecenoic acid, (Z)- (8CI), (9Z)-Tetradeca-9-enoic acid, (Z)-9-Tetradecenoic acid, 9(Z)-Tetradecenoic acid, 9-cis-Tetradecenoic acid, cis-9-Tetradecenoic acid, cis-Δ9-Tetradecenoic acid, Myristoleic acid, Myristolenic acid, Oleomyristic acid, 9(Z)-Tetradecenoic acid, 9-Tetradecenoic acid, (Z)-, Z-9-Tetradecenoic acid, (9Z)-9-Tetradecenoic acid, (Z)-tetradec-9-enoic acid

C14:1 Myristoleic Acid is a monounsaturated fatty acid with a 14-carbon chain and one double bond, commonly identified as C14:1.
C14:1 Myristoleic Acid occurs naturally in certain plant and animal fats, particularly in nutmeg seed oil and some marine oils.
C14:1 Myristoleic Acid belongs to the omega-5 fatty acid family and is valued for its distinctive chemical structure.

C14:1 Myristoleic Acid appears as an oily liquid at room temperature and exhibits typical fatty acid characteristics such as hydrophobicity and lubricity.
C14:1 Myristoleic Acid is used mainly as a specialty raw material rather than a bulk commodity due to its limited natural availability.

C14:1 Myristoleic Acid plays an important role in both industrial and research applications where specific chain length and unsaturation are required.
C14:1 Myristoleic Acid, with the CAS number 544-64-9, is a monounsaturated fatty acid that is classified as a long-chain fatty acid.

C14:1 Myristoleic Acid is an unsaturated fatty acid with a 14-carbon chain and one double bond located at the ninth carbon from the methyl end, which is characteristic of its classification as a cis-9-tetradecenoic acid.
C14:1 Myristoleic Acid is typically found in various natural sources, including certain plant oils and animal fats.

C14:1 Myristoleic Acid is known for its potential health benefits, including anti-inflammatory properties and its role in lipid metabolism.
The presence of the double bond contributes to its fluidity and reactivity compared to saturated fatty acids.
Its molecular formula is C14H26O2, and C14:1 Myristoleic Acid has a relatively low melting point, which is typical for unsaturated fatty acids.

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 C14:1 Myristoleic Acid is the seed oil from plants of the genus Myristicaceae, comprising up to 30 per cent of the oil in some species.

C14:1 Myristoleic Acid is a monounsaturated fatty acid with a 14-carbon chain and one double bond.
C14:1 Myristoleic Acid's systematic IUPAC name is (9Z)-tetradec-9-enoic acid, and it is an omega-5 fatty acid.
C14:1 Myristoleic Acid is biosynthesized from myristic acid by desaturation, but is relatively uncommon in nature.

C14:1 Myristoleic Acid is found naturally in plant seed oils (such as in the Myristicaceae family) and in some animal fats and oils.
C14:1 Myristoleic Acid also appears in extracts like Serenoa repens (saw palmetto), where it can exhibit biological activity.
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.
C14:1 Myristoleic Acid has been reported in Hoya crassipes, Hoya pseudolanceolata, and other organisms with data available.
C14:1 Myristoleic Acid is a metabolite found in or produced by Saccharomyces cerevisiae.

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 colorless liquid.
C14:1 Myristoleic Acid is found in fatof some seeds and in fish oil.

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.
C14:1 Myristoleic Acid is a type of fatty acid that was found to be significantly higher in diets containing 0.05% or 0.1% cinnamon essential oil compared to a basal diet.

USES and APPLICATIONS of C14:1 MYRISTOLEIC ACID:
C14:1 Myristoleic Acid is a mono-unsaturated medium-chain fatty acid used as a model substrate for enzymes such as the cytochrome P450 enzyme CYP102D1; the aromatic peroxygenase from Agrocybe aegerita and oleate hydratase from Lysinibacillus fusiformis.
C14:1 Myristoleic Acid is used as an intermediate in the chemical and oleochemical industries for the synthesis of specialty esters and surfactants.

C14:1 Myristoleic Acid finds application in hair care formulations, where it contributes to conditioning and shine.
In the pharmaceutical and nutraceutical fields, C14:1 Myristoleic Acid has been studied for its potential anti-inflammatory and joint health–supporting properties.

C14:1 Myristoleic Acid is used as a raw material in the production of soaps and cleansing products, contributing to mildness and foam characteristics.
C14:1 Myristoleic Acid is applied in the manufacture of specialty lubricants and metalworking fluids because of its natural lubricity.

C14:1 Myristoleic Acid is used in research and development as a reference fatty acid for biochemical and lipid metabolism studies.
In industrial formulations, C14:1 Myristoleic Acid can act as a processing aid to improve compatibility between oil-based components.
C14:1 Myristoleic Acid is also used in the preparation of bio-based and biodegradable products as part of sustainable material formulations.

C14:1 Myristoleic Acid can be used in various applications, including food, cosmetics, and pharmaceuticals, due to its emollient properties.
Additionally, C14:1 Myristoleic Acid serves as a precursor for the synthesis of other bioactive compounds.
C14:1 Myristoleic Acid induces apoptosis and necrosis in human prostrate cancer cell LNCaP, and is of a potential for developing an attractive new tool for the treatment of prostrate cancer.

Lipid research and analysis: C14:1 Myristoleic Acid is used as a reference or standard in lipidomics and analytical chemistry.
Biological studies: C14:1 Myristoleic Acid is investigated for effects on cell signaling, apoptosis, and lipid metabolism.
Cosmetic / personal care ingredient: C14:1 Myristoleic Acid is sometimes included in formulations for texture or fatty acid content (not a major common ingredient).
Chemical intermediate: C14:1 Myristoleic Acid is used in organic synthesis and derivatization studies.

BIOLOGICAL ACTIVITY of C14:1 MYRISTOLEIC ACID:
C14:1 Myristoleic Acid has been studied for cytotoxic effects in certain cell culture models, including inducing apoptosis in prostate cancer cells (LNCaP), and is present in extracts like saw palmetto.

FUNCTIONAL CHARACTERISTICS & BENEFITS of C14:1 MYRISTOLEIC ACID:
While not a widely used commercial fatty acid like oleic or linoleic acid, C14:1 Myristoleic Acid:
C14:1 Myristoleic Acid has lipophilic characteristics due to its long carbon chain and unsaturation.
C14:1 Myristoleic Acid is part of cell membrane lipid composition in organisms that synthesize it.
C14:1 Myristoleic Acid exhibits biological activity in some cellular pathways.

PHYSICAL and CHEMICAL PROPERTIES of C14:1 MYRISTOLEIC ACID:
IUPAC Name: (9Z)-tetradec-9-enoic acid
Common Name: Myristoleic acid
CAS Number: 544-64-9
EC / EINECS Number: 208-876-8
PubChem CID: 5281119
Molecular Formula: C₁₄H₂₆O₂
Molecular Weight: 226.35 g/mol
SMILES: CCCC/C=C/CCCCCCCC(=O)O
InChIKey: YWWVWXASSLXJHU-WAYWQWQTSA-N

Lipid Number (common in lipidomics): FA(14:1n-5)
Physical State & Appearance:
State at Room Temperature: Colorless to light yellow liquid (typical)
Odor: Fatty / Waxy / Oily profile (various source descriptions)
Key Properties:
Molecular Formula: C₁₄H₂₆O₂
Molecular Weight: 226.35 g/mol
Density: ~0.9 g/cm³ at 20–25 °C
Melting Point: ~ −4.5 °C to −4 °C

Boiling Point: ~144 °C at 0.6 mm Hg (reduced pressure; normal bp is much higher ~300+ °C)
Refractive Index: ~ n²⁰/D 1.4562
Flash Point: ~62 °C (some sources vary depending on conditions)
Solubility: Slightly soluble in organic solvents like benzenes, methanol, chloroform
Solubility: Practically insoluble in water
Predicted pKa: ~4.78 (acidic carboxyl group)
LogP (partition coefficient): ~5.1–5.4 (highly lipophilic)
Molecular Weight: 226.35 g/mol

XLogP3: 5.1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 11
Exact Mass: 226.193280068 Da
Monoisotopic Mass: 226.193280068 Da
Topological Polar Surface Area: 37.3 Å²
Heavy Atom Count: 16
Formal Charge: 0

Complexity: 185
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

Chemical formula: C14H26O2
Molar mass: 226.360 g•mol−1
CBNumber: CB2447081
Molecular Formula: C14H26O2
Molecular Weight: 226.35
MDL Number: MFCD00004436
MOL File: 544-64-9.mol

Melting point: −4.5-−4 °C(lit.)
Boiling point: 144 °C0.6 mm Hg(lit.)
Density: 0.9 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.4562(lit.)
Flash point: 62 °C
Storage temp.: -20°C
Solubility: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
Form: Liquid

pKa: 4.78±0.10(Predicted)
Color: Colourless
Biological source: plant
Cosmetics Ingredients Functions: NOT REPORTED
InChI: InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
InChIKey: YWWVWXASSLXJHU-WAYWQWQTSA-N
SMILES: C(O)(=O)CCCCCCC/C=CCCCC
LogP: 5.383 (est)

FDA UNII: RF23WGD123
EPA Substance Registry System: 9-Tetradecenoic acid, (9Z)- (544-64-9)
UNSPSC Code: 85151701
NACRES: NA.25
Linear Formula: CH3(CH2)3CH=CH(CH2)7CO2H
CAS Number: 544-64-9
Molecular Weight: 226.36
NACRES: NA.25
PubChem Substance ID: 24896849

UNSPSC Code: 12352211
EC Number: 208-876-8
MDL number: MFCD00004436
ECHA EINECS - REACH Pre-Reg: 208-876-8
FDA UNII: RF23WGD123
Nikkaji Web: J11.362J
MDL: MFCD00004436
XlogP3: 5.10 (est)
Molecular Weight: 226.35962000

Formula: C14 H26 O2
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 338.00 to 339.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.000017 mmHg @ 25.00 °C. (est)
Flash Point: 404.00 °F. TCC ( 206.50 °C. ) (est)
logP (o/w): 5.383 (est)
Soluble in: alcohol
Soluble in: water, 0.9431 mg/L @ 25 °C (est)

Insoluble in: water
Molecular Formula: C14H26O2
Formula Weight: 226.4
Purity: ≥95%
Formulation: (Request formulation change) A 100 mg/ml solution in ethanol
Solubility: DMF: 3 mg/ml
Solubility: DMSO: 2 mg/ml
Solubility: Ethanol: Miscible
Solubility: PBS (pH 7.2): 2 mg/ml

SMILES: OC(CCCCCCC/C=CCCCC)=O
InChi Code: InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
InChi Key: YWWVWXASSLXJHU-WAYWQWQTSA-N
Side Chain Carbon Sum: 14:1
Formula: C14H26O2
InChI: InChI=1/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
InChI key: InChIKey=YWWVWXASSLXJHU-WAYWQWQTSA-N
SMILES: C(CC/C=CCCCC)CCCCC(O)=O

FIRST AID MEASURES of C14:1 MYRISTOLEIC ACID:
-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 C14:1 MYRISTOLEIC ACID:
-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 C14:1 MYRISTOLEIC ACID:
-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 C14:1 MYRISTOLEIC ACID:
-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 C14:1 MYRISTOLEIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of C14:1 MYRISTOLEIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available