Myristoleic acid

Names

[ CAS No. ]:
544-64-9

[ Name ]:
Myristoleic acid

[Synonym ]:
cis-9-tetradecenoic acid
cis-δ(9)-tetradecenoic acid
(9Z)-9-Tetradecenoic acid
Myristoleic acid (14:1(n-5))
9-Tetradecenoic acid, (9Z)-
tetradecenoic acid
(9Z)-Tetradec-9-enoic acid
Z-9-tetradecenoic acid
(9Z)-Tetradecenoic acid
9-Tetradecenoic acid, (Z)-
Z-9-octadecene-4-olide
MFCD00004436
9Z-tetradecenoic acid
Myristoleate
EINECS 208-876-8
Myristoleic acid

Biological Activity

[Description]:

Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Inflammation/Immunology

[In Vitro]

Myristoleic acid induces both apoptosis (100 μg/mL, 89.5%) and necrosis (100 μg/mL, 81.8%) in LNCaP cells[1]. Myristoleic acid inhibited RANKL-induced osteoclast formation in vitro, especially, at later stages of differentiation[2]. Cell Proliferation Assay[1] Cell Line: Human prostatic carcinoma LNCaP cells. Concentration: 0, 50, 100, 150, 200, 250 μg/mL. Incubation Time: 24 h. Result: When LNCaP cells were treated with 130 μg/mL extract or 100 μg/mL myristoleic acid for 24 hr, the proportion of apoptotic cells was 16.5 and 8.8%, and that of necrotic one was 46.8 and 81.8%, respectively.

[In Vivo]

Myristoleic acid (2 mg/kg, IP every 24 h for 4 days) prevents RANKL-induced bone loss and osteoclast formation in mice[2]. Animal Model: C57BL/6 mice at 5 weeks[2]. Dosage: 0.2, 2 mg/kg Administration: IP every 24 h for 4 days. Result: Co-administration of myristoleic acid suppressed generation of TRAP-positive osteoclasts induced by sRANKL and attenuated the increases in osteoclastic indices of Oc.S/BS, N.Oc/B. Pm and ES/BS in a dose-dependent manner.

[References]

[1]. Xiaoyan Gao, et al. Ozone initiated heterogeneous oxidation of unsaturated carboxylic acids by ATR-FTIR spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2019 May 5;214:177-183.

[2]. Jun-Oh Kwon, et al. 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.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
338.9±0.0 °C at 760 mmHg

[ Melting Point ]:
-4.5--4ºC(lit.)

[ Molecular Formula ]:
C₁₄H₂₆O₂

[ Molecular Weight ]:
226.355

[ Flash Point ]:
206.5±14.4 °C

[ Exact Mass ]:
226.193283

[ PSA ]:
37.30000

[ LogP ]:
5.57

[ Appearance of Characters ]:
Liquid

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.465

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NA 1993 / PGIII

[ WGK Germany ]:
3

[ HS Code ]:
2916190090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2916190090

[ Summary ]:
2916190090 unsaturated acyclic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:6.5%。general tariff:30.0%

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