13-Methyltetradecanoic acid

Names

[ Name ]:
13-Methyltetradecanoic acid

[Synonym ]:
13-Methylmyristic acid
13-METHYLTETRADECANOIC ACID
13-Methyltetradecanoic acid

Biological Activity

[Description]:

13-Methyltetradecanoic acid (13-MTD), a saturated branched-chain fatty acid with potent anticancer effects. 13-Methyltetradecanoic acid induces apoptosis in many types of human cancer cells[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[In Vitro]

13-Methyltetradecanoic acid (13-MTD; 0-140 μg/mL; 12-24 hours) inhibits cell viability and proliferation in human bladder cancer cells by inducing apoptosis[1]. 13-Methyltetradecanoic acid (13-MTD; 70 μg/mL; 2-48 hours) treatments results in significant accumulation of cells with sub-G1 DNA content in a time-dependent manner, with the proportion of sub-G1 phase DNA content ranging from 9.25% to 85.3% over 2-48 hours[1]. 13-Methyltetradecanoic acid (13-MTD; 70 μg/mL; 2-24 hours) down-regulates Bcl-2 and up-regulates Bax. This promotes mitochondrial dysfunction, leading to the release of cytochrome c from the mitochondria to the cytoplasm, as well as the proteolytic activation of caspases. 13-Methyltetradecanoic acid down-regulates AKT phosphorylation and activates phosphorylation of p38 and c-Jun N-terminal kinase (JNK)[1]. Cell Viability Assay[1] Cell Line: Bladder cancer cell lines T24, 5637, and UM-UC-3 Concentration: 0 μg/mL, 35 μg/mL, 70 μg/mL, 105 μg/mL, and 140 μg/mL Incubation Time: 12 hours, 24 hours Result: Inhibition of cell viability in a dose- and time-dependent manner. Cell Cycle Analysis[1] Cell Line: Bladder cancer cell lines T24, 5637, and UM-UC-3 Concentration: 70 μg/mL Incubation Time: 2 hours, 8 hours, 24 hours, or 48 hours Result: Resulted in significant accumulation of cells with sub-G1 DNA content in a time-dependent manner. Western Blot Analysis[1] Cell Line: T24, 5637, and UM-UC-3 cells Concentration: 70 μg/mL Incubation Time: 2 hours, 8 hours, 24 hours Result: Down-regulated Bcl-2 and up-regulated Bax, and down-regulated AKT phosphorylation and activated phosphorylation of p38 and c-Jun N-terminal kinase (JNK).

[In Vivo]

13-Methyltetradecanoic acid (13-MTD; 70 mg/kg/day; oral gavage; daily; for 30 days) significantly suppresses tumor growth in a xenograft model[2]. Animal Model: BALB/C nude mice injected with Jurkat lymphoma cells[2] Dosage: 70 mg/kg/day Administration: Oral gavage; daily; for 30 days Result: Effectively inhibited the growth in vivo in a xenograft model.

[References]

[1]. Tianxin Lin, et al. 13-Methyltetradecanoic acid induces mitochondrial-mediated apoptosis in human bladder cancer cells. Urol Oncol. May-Jun 2012;30(3):339-45.

[2]. Qingqing Cai, et al. 13-methyltetradecanoic acid exhibits anti-tumor activity on T-cell lymphomas in vitro and in vivo by down-regulating p-AKT and activating caspase-3. PLoS One. 2013 Jun 7;8(6):e65308.

Chemical & Physical Properties

[ Density]:
0.894 g/cm3

[ Boiling Point ]:
355.5ºC at 760 mmHg

[ Molecular Formula ]:
C₁₅H₃₀O₂

[ Molecular Weight ]:
242.40

[ Flash Point ]:
197.4ºC

[ Exact Mass ]:
242.22500

[ PSA ]:
37.30000

[ LogP ]:
5.01810

[ Vapour Pressure ]:
5.19E-06mmHg at 25°C

[ Index of Refraction ]:
1.451

[ Storage condition ]:
2-8°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 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2915900090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2915900090

[ Summary ]:
2915900090 other saturated acyclic monocarboxylic acids and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:5.5% General tariff:30.0%

Articles

Melanogenesis of methyl myristate loaded niosomes in B16F10 melanoma cells.

J. Biomed. Nanotechnol. 9(4) , 626-38, (2013)

The objective of this study was to compare the charge effect of methyl myristate loaded in neutral (Brij 72/cholesterol at 7:3), cationic (Brij 72/cholesterol/dimethyl dioctadecyl ammonium bromide at ...

Methyl-branched poly(hydroxyalkanoate) biosynthesis from 13-methyltetradecanoic acid and mixed isostearic acid isomer substrates.

Appl. Microbiol. Biotechnol. 85 , 359-370, (2009)

Pseudomonas resinovorans, a known medium-chain-length (mcl-) poly(hydroxyalkanoate) (PHA) producer, was grown on 13-methyltetradecanoic acid (13-MTDA) and a mixture of isostearic acid (IA) isomers to ...

13-Methyltetradecanoic acid induces mitochondrial-mediated apoptosis in human bladder cancer cells.

Urol. Oncol. 30(3) , 339-45, (2010)

13-Methyltetradecanoic acid (13-MTD), a saturated branched-chain fatty acid purified from soy fermentation products, is known to induce apoptosis in many types of human cancer cells. This study was de...

Related Compounds

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