Myristoleic acid

Modify Date: 2024-01-04 11:05:14

Myristoleic acid Structure
Myristoleic acid structure
Common Name Myristoleic acid
CAS Number 544-64-9 Molecular Weight 226.355
Density 0.9±0.1 g/cm3 Boiling Point 338.9±0.0 °C at 760 mmHg
Molecular Formula C14H26O2 Melting Point -4.5--4ºC(lit.)
MSDS Chinese USA Flash Point 206.5±14.4 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Myristoleic acid


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

 Names

Name Myristoleic acid
Synonym More Synonyms

 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
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

 Safety Information

Symbol GHS07
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

~77%

Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Journal of Pharmaceutical Sciences, , vol. 83, # 3 p. 296 - 299

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Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Journal of Chemical Ecology, , vol. 21, # 10 p. 1495 - 1510

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Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Journal of the Chemical Society, , p. 775 - 778

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Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Journal of the Chemical Society, , p. 775 - 778

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Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Journal of the Chemical Society, , p. 775 - 778

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Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Journal of the Chemical Society, , p. 671,674

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Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Chemische Berichte, , vol. 108, # 11 p. 3582 - 3595

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Myristoleic acid Structure

Myristoleic acid

CAS#:544-64-9

Literature: Chemische Berichte, , vol. 108, # 11 p. 3582 - 3595

 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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 Synonyms

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
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