| Identification | Back Directory | [Name]
8(Z),10(E),12(Z)-OCTADECATRIENOIC ACID | [CAS]
28872-28-8 | [Synonyms]
JACARIC ACID
8(Z),10(E),12(Z)-OCTADECATRIENOIC ACID
(8E,10Z,12Z)-Octadeca-8,10,12-trienoic acid | [Molecular Formula]
C18H30O2 | [MDL Number]
MFCD05864027 | [MOL File]
28872-28-8.mol | [Molecular Weight]
278.43 |
| Chemical Properties | Back Directory | [Boiling point ]
423.4±24.0 °C(Predicted) | [density ]
0.924±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C, Light sensitive | [solubility ]
Ethanol (Soluble) | [form ]
Colourless Solution | [pka]
4.77±0.10(Predicted) | [Stability:]
Light Sensitive |
| Hazard Information | Back Directory | [Description]
Jacaric acid is a conjugated polyunsaturated fatty acid first isolated from seeds of Jacaranda plants. Structurally, it is an 18-carbon ω-6 triene isomer of γ-linolenic acid . Jacaric acid induces cell cycle arrest and apoptosis in a variety of cancer cell lines (GI50 = 1-5 μM). It increases the production of reactive oxygen species, and cytotoxicity is abolished by the antioxidant α-tocopherol, suggesting that apoptosis results from oxidative stress. Jacaric acid is metabolized in vivo to conjugated linoleic acid (Item No. 90140), which is also cytotoxic to cancer cells. 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. | [Uses]
8(Z),10(E),12(Z)-Octadecatrienoic Acid, is a conjugated Linoleic Acid, a compound that has reported to exhibit anticarcinogenic activity. Also a potent antioxidant. | [Uses]
Jacaric Acid (10mg/mL in Ethanol) is a conjugated polyunsaturated fatty acid first isolated from seeds of Jacaranda plants. | [Definition]
ChEBI: 8Z,10E,12Z-octadecatrienoic acid is an octadecatrienoic acid. | [in vivo]
Jacaric acid (1 mg/day/mouse, p.o. for 36 days) exhibits antitumor activity in DLD-1 transplanted athymic nude mice, without significant toxicity[2]. | Animal Model: | DLD-1 xenograft athymic nude mice[2] | | Dosage: | 1 mg/mouse | | Administration: | p.o. for 36 days | | Result: | Reduced tumor volume without significant weight loss in body and liver. |
| [References]
[1] J MIRANDA. A comparison between CLNA and CLA effects on body fat, serum parameters and liver composition.[J]. Journal of physiology and biochemistry, 2009, 65 1: 25-32. DOI: 10.1007/bf03165966
[2] JIHANE GASMI J. T S. Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure–activity study[J]. Phytomedicine, 2013, 20 8: Pages 734-742. DOI: 10.1016/j.phymed.2013.01.012
[3] MASAO YAMASAKI. Induction of apoptotic cell death in HL-60 cells by jacaranda seed oil derived fatty acids.[J]. Journal of oleo science, 2013, 62 11: 925-932. DOI: 10.5650/jos.62.925
[4] WAI NAM LIU Kwok N L. Jacaric acid inhibits the growth of murine macrophage-like leukemia PU5-1.8 cells by inducing cell cycle arrest and apoptosis.[J]. Cancer Cell International, 2015, 15: 90. DOI: 10.1186/s12935-015-0246-5
[5] T.D. SHULTZ . Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cells[J]. Cancer letters, 1992, 63 2: Pages 125-133. DOI: 10.1016/0304-3835(92)90062-z
[6] NAHOKO SHINOHARA. jacaric acid, a linolenic acid isomer with a conjugated triene system, reduces stearoyl-CoA desaturase expression in liver of mice.[J]. Journal of oleo science, 2012, 61 8: 433-441. DOI: 10.5650/jos.61.433 |
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