Jacaric Acid (CAS 28872-28-8) | Cayman Chemical
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Jacaric Acid

Item № 16036
CAS № 28872-28-8
Purity ≥95%
product image
                (CAS 28872-28-8)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $99.00 0.00
     5 mg $446.00 0.00
     10 mg $792.00 0.00

Pricing updated 2018-11-19. Prices are subject to change without notice.

Description
Synonyms
  • 8(Z),10(E),12(Z)-Octadecatrienoic Acid

Jacaric acid is a conjugated polyunsaturated fatty acid first isolated from seeds of Jacaranda plants.1 Structurally, it is an 18-carbon ω-6 triene isomer of γ-linolenic acid (Item No. 90220). Jacaric acid induces cell cycle arrest and apoptosis in a variety of cancer cell lines (GI50 = 1-5 µM).2,3,4 It increases the production of reactive oxygen species, and cytotoxicity is abolished by the antioxidant α-tocopherol, suggesting that apoptosis results from oxidative stress.3,4 Jacaric acid is metabolized in vivo to conjugated linoleic acid (Item No. 90140), which is also cytotoxic to cancer cells.5 Jacaric acid inhibits cyclooxygenase-1 in vitro (Ki = 1.7 µM) and, with long term feeding, decreases stearoyl-CoA desaturase expression and activity in mice.6,7

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Technical Information
Formal Name
8Z,10E,12Z-octadecatrienoic acid
CAS Number
28872-28-8
Synonyms
  • 8(Z),10(E),12(Z)-Octadecatrienoic Acid
Molecular Formula
C18H30O2
Formula Weight
278.4
Purity
≥95%
Formulation
A crystalline solid
λmax
273, 284 nm
SMILES
CCCCC/C=C\C=C\C=C/CCCCCCC(O)=O
InChI Code
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10-
InChI Key
DQGMPXYVZZCNDQ-KDQYYBQISA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Miranda, J., Fernández-Quintela, A., Macarulla, M.T., et al. A comparison between CLNA and CLA effects on body fat, serum parameters and liver composition J.Physiol.Biochem. 65(1), 25-32 (2009).

2. Gasmi, J., and Sanderson, J.T. Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: A mechanistic and 3-D structure-activity study Phytomedicine 20(8-9), 734-742 (2013).

3. Yamasaki, M., Motonaga, C., Yokoyama, M., et al. Induction of apoptotic cell death in HL-60 cells by jacaranda seed oil derived fatty acids J.Oleo Sci. 62(11), 925-932 (2013).

4. Liu, W.N., and Leung, K.N. Jacaric acid inhibits the growth of murine macrophage-like leukemia PU5-1.8 cells by inducing cell cycle arrest and apoptosis Cancer Cell Int. 15, (2015).

5. Shultz, T.D., Chew, B.P., Seaman, W.R., et al. Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cells Cancer Letters 63, 125-133 (1992).

6. Mashhadi, Z., Boeglin, W.E., and Brash, A.R. Robust inhibitory effects of conjugated linolenic acids on a cyclooxygenase-related linoleate 10S-dioxygenase: Comparison with COX-1 and COX-2 Biochim.Biophys.Acta. 1851(10), 1346-1352 (2015).

7. Shinohara, N., Ito, J., Tsuduki, T., et al. Jacaric acid, a linolenic acid isomer with a conjugated triene system, reduces stearoyl-CoA desaturase expression in liver of mice J.Oleo Sci. 61(8), 433-441 (2012).

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