cis-Vaccenic acid

Names

[ CAS No. ]:
506-17-2

[ Name ]:
cis-Vaccenic acid

[Synonym ]:
(Z)-11-octadecenoic acid
cis-Vaccenic acid
11-Octadecenoic acid, (Z)-
11-cis-Octadecenoic acid
cis-11-Octadecenoic acid
MFCD00063187
11(Z)-Octadecenoic acid
11-Octadecenoic acid, (11Z)-
(11Z)-11-Octadecenoic acid
asclepic acid
Vaccenic acid
11Z-Octadecenoic acid
(11Z)-Octadec-11-enoic acid
(Z)-vaccenic acid
cis-11-Vaccenic acid

Biological Activity

[Description]:

cis-Vaccenic acid, the antiviral extract from Rhodopseudomonas capsulate and the predominant active component of Rhodopseudomonas capsulate[1], acts a potential fetal hemoglobin inducer[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

cis-Vaccenic acid (CVA) (50 μM, 70 μM and 100 μM) induces differentiation and up-regulates gamma globin synthesis in K562, JK1 and transgenic mice erythroid progenitor stem cells[2]. cis-Vaccenic acid (50 μM) also increased the percentage of benzidine positive JK-1 cell[2]. Cell Differentiation Assay[2] Cell Line: K562 cells Concentration: 50 μM, 70 μM and 100 μM Incubation Time: 48 and 120 hours Result: Induced differentiation appeared to be concentration dependent in K562 cells with 50 μM CVA being the most effective concentration with more than 20% of the K562 cells showing positive for Benzidine stain after 48 h of incubation with CVA.

[References]

[1]. H Hirotani, et al. Inactivation of T5 phage by cis-vaccenic acid, an antivirus substance from Rhodopseudomonas capsulata, and by unsaturated fatty acids and related alcohols. FEMS Microbiol Lett. 1991 Jan 1;61(1):13-7.

[2]. Idowu A Aimola, et al. Cis-vaccenic acid induces differentiation and up-regulates gamma globin synthesis in K562, JK1 and transgenic mice erythroid progenitor stem cells. Eur J Pharmacol. 2016 Apr 5;776:9-18.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
398.2±11.0 °C at 760 mmHg

[ Melting Point ]:
14-15ºC(lit.)

[ Molecular Formula ]:
C₁₈H₃₄O₂

[ Molecular Weight ]:
282.461

[ Flash Point ]:
295.0±14.4 °C

[ Exact Mass ]:
282.255890

[ PSA ]:
37.30000

[ LogP ]:
7.70

[ Appearance of Characters ]:
oil

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.467

[ 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 ]:
NONH for all modes of transport

[ 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%

Articles

Characterization of Shrimp Oil from Pandalus borealis by High Performance Liquid Chromatography and High Resolution Mass Spectrometry.

Mar. Drugs 13 , 3849-76, (2015)

Northern shrimp (Pandalus borealis) oil, which is rich in omega-3 fatty acids, was recovered from the cooking water of shrimp processing facilities. The oil contains significant amounts of omega-3 fat...

Palmitoleic (16:1 cis-9) and cis-vaccenic (18:1 cis-11) acid alter lipogenesis in bovine adipocyte cultures.

Lipids 47(12) , 1143-53, (2012)

Our objectives were to: (1) confirm elongation products of palmitoleic acid (16:1 cis-9) elongation in vitro using stable isotopes and (2) evaluate if exogenous supplementation of palmitoleic acid, el...

Red blood cell membrane concentration of cis-palmitoleic and cis-vaccenic acids and risk of coronary heart disease.

Am. J. Cardiol. 110(4) , 539-44, (2012)

Although previous studies have suggested associations between plasma palmitoleic acid and coronary heart disease (CHD) risk factors, including blood pressure, inflammation, and insulin resistance, lit...