Basic information
- CAS
544-64-9- Standard SMILES
CCCC/C=C\CCCCCCCC(=O)O- InChIKey
YWWVWXASSLXJHU-WAYWQWQTSA-N- Molecular formula
- C14H26O2
- Average molar mass
- 226.35 g/mol
- Monoisotopic mass
- 226.19328007
Overview
Myristoleic acid is a tetradecenoic acid in which the double bond is at the 9-10 position and has Z configuration. Myristoleic acid has been isolated from Serenoa repens and has cytotoxic and apoptosis-inducing effects. It has a role as an apoptosis inducer, a plant metabolite and an EC 3.1.1.1 (carboxylesterase) inhibitor. It is a long-chain fatty acid and a tetradecenoic acid. It is a conjugate acid of a myristoleate.
Names & identifiers
- Preferred name
- Myristoleic Acid
- IUPAC
- (Z)-tetradec-9-enoic acid
- English name
- MYRISTOLEIC ACID
- Molecular formula
- C14H26O2
- Molecular weight
- 226.35
Names & synonyms
Myristoleic acid544-64-9(Z)-Tetradec-9-enoic acid9Z-tetradecenoic acidcis-9-tetradecenoic acid9-Tetradecenoic acid, (9Z)-9-Tetradecenoic acid(9Z)-Tetradecenoic acidcis-tetradec-9-enoic acidRF23WGD123DTXSID5041568CHEBI:27781
Show more names
C14:1 (CIS-9) ACIDMYRISTOLEIC ACID 99%(z)-9-tetradecenoicaci(Z)-9-TetradecenoicacidMyristoleic Acid(C14:1)9(Z)-Tetradecanoic acid
14:1(N-5)RefChem:160412Fatty Acid 14:1 n-5DTXCID3021568208-876-8(9Z)-tetradec-9-enoic acidMyristolenic acidsodium myristoleate
Database identifiers
- CAS
544-64-9- PubChem CID
- 5281119
- DTXSID
DTXSID5041568- ChEMBL
CHEMBL456732- ChEBI
CHEBI:27781- UNII
- RF23WGD123
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 11
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 185
Experimental & physicochemical properties
Lipids
Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
Physical Description
Liquid
Liquid
Collision Cross Section159.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
Physicochemical properties
- Melting point
- 4.5 · −4.5-−4 °C(lit.)
- Boiling point
- 144 °C0.6 · 144 °C0.6 mm Hg(lit.)
- Density
- 0.9 g/mL · 0.9 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.4562(lit.)
- Flash point
- 62 °C · 62 °C
- storage temp.
- -20 °C · -20°C
- solubility
- Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
- form
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 82.1% (569 of 693) of all reports.
Warning
H315 (13.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 693 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
9-Tetradecenoic acid, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Tetradecenoic acid, (9Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
9-Tetradecenoic acid, (9Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
EPA Safer ChemicalChemical: Myristoleic acid
Hazard Classes and CategoriesSkin Irrit. 2 (13.9%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- NA 1993 / PGIII
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
Chemistry & industry
Pharmacology
Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular
Uses & manufacturing
U.S. Production2023: 1,000,000 - <5,000,000 lb
Consumer UsesBinder
Industry UsesAnti-static agent
Household ProductsInformation on 2 consumer products that contain Myristoleic acid in the following categories is provided:
Use Classification
EPA Safer Chemical Functional Use Classes -> Surfactants
Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern
General Manufacturing Information
Plastics Product Manufacturing
9-Tetradecenoic acid, (9Z)-: ACTIVE
Applications
UsesMyristoleic 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.
Upstream & downstream products
Downstream products
Suppliers94 total
Related reactions
2 records
Compound notes
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