Myristoleic Acid | CAS#544-64-9 | Apoptosis inducer

MedKoo Cat#: 112125 | Name: Myristoleic Acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Myristoleic acid induces apoptosis and necrosis in human prostate cancer LNCaP cells.

Chemical Structure

Myristoleic Acid

CAS#544-64-9

Theoretical Analysis

MedKoo Cat#: 112125

Name: Myristoleic Acid

CAS#: 544-64-9

Chemical Formula: C14H26O2

Exact Mass: 226.1933

Molecular Weight: 226.36

Elemental Analysis: C, 74.29; H, 11.58; O, 14.14

Price and Availability

Size	Price	Availability
50mg	USD 280.00	2 Weeks
100mg	USD 530.00	2 Weeks
250mg	USD 900.00	2 Weeks

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Related CAS #

No Data

Synonym

Myristoleic Acid; cis-9-Tetradecenoate; Oleomyristic Acid

IUPAC/Chemical Name

(Z)-tetradec-9-enoic acid

InChi Key

YWWVWXASSLXJHU-WAYWQWQTSA-N

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-

SMILES Code

OC(CCCCCCC/C=C\CCCC)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	3.0	13.25
	DMSO	2.5	11.04
	PBS (pH:7.2)	2.0	8.84

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 226.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Quan LH, Zhang C, Dong M, Jiang J, Xu H, Yan C, Liu X, Zhou H, Zhang H, Chen L, Zhong FL, Luo ZB, Lam SM, Shui G, Li D, Jin W. Myristoleic acid produced by enterococci reduces obesity through brown adipose tissue activation. Gut. 2020 Jul;69(7):1239-1247. doi: 10.1136/gutjnl-2019-319114. Epub 2019 Nov 19. PMID: 31744910. 2: Kwon JO, Jin WJ, Kim B, Kim HH, Lee ZH. Myristoleic acid inhibits osteoclast formation and bone resorption by suppressing the RANKL activation of Src and Pyk2. Eur J Pharmacol. 2015 Dec 5;768:189-98. doi: 10.1016/j.ejphar.2015.10.053. Epub 2015 Oct 31. PMID: 26528796. 3: Choi YK, Kang JI, Hyun JW, Koh YS, Kang JH, Hyun CG, Yoon KS, Lee KS, Lee CM, Kim TY, Yoo ES, Kang HK. Myristoleic Acid Promotes Anagen Signaling by Autophagy through Activating Wnt/β-Catenin and ERK Pathways in Dermal Papilla Cells. Biomol Ther (Seoul). 2021 Mar 1;29(2):211-219. doi: 10.4062/biomolther.2020.169. PMID: 33518533; PMCID: PMC7921852. 4: Kim YG, Lee JH, Lee J. Antibiofilm activities of fatty acids including myristoleic acid against Cutibacterium acnes via reduced cell hydrophobicity. Phytomedicine. 2021 Oct;91:153710. doi: 10.1016/j.phymed.2021.153710. Epub 2021 Aug 18. PMID: 34461422. 5: Iguchi K, Okumura N, Usui S, Sajiki H, Hirota K, Hirano K. Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Prostate. 2001 Apr;47(1):59-65. doi: 10.1002/pros.1047. PMID: 11304730. 6: Hannauer M, Schäfer M, Hoegy F, Gizzi P, Wehrung P, Mislin GL, Budzikiewicz H, Schalk IJ. Biosynthesis of the pyoverdine siderophore of Pseudomonas aeruginosa involves precursors with a myristic or a myristoleic acid chain. FEBS Lett. 2012 Jan 2;586(1):96-101. doi: 10.1016/j.febslet.2011.12.004. Epub 2011 Dec 9. PMID: 22172280. 7: Kong CY, Mori M, Funazukuri T, Kagei S. Measurements of binary diffusion coefficients, retention factors and partial molar volumes for myristoleic acid and its methyl ester in supercritical carbon dioxide. Anal Sci. 2006 Nov;22(11):1431-6. doi: 10.2116/analsci.22.1431. PMID: 17099274. 8: Liao S, Lin J, Dang MT, Zhang H, Kao YH, Fukuchi J, Hiipakka RA. Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid. Arch Dermatol Res. 2001 Apr;293(4):200-5. doi: 10.1007/s004030000203. PMID: 11380153.