Jacaric Acid

CAT: 0931-T36099-02Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0931-T36099-02Size:5 mg

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CAS Number

28872-28-8

Target

Others, Apoptosis

Related Pathways

Apoptosis, Others

Bioactivity

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 , 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.

Smiles

CCCCC\C=C/C=C/C=C\CCCCCCC(O)=O

Molecular Formula

C18H30O2

Molecular Weight

278.436

Shipping Conditions

Ice Packs

Storage Temperature

-20°C

Chemical Information

Jacaric acid

8Z,10E,12Z-octadecatrienoic acid is an octadecatrienoic acid.

CAS Number	28872-28-8
PubChem CID	5282817
IUPAC Name	(8Z,10E,12Z)-octadeca-8,10,12-trienoic acid
Molecular Formula	C18H30O2
Molecular Weight	278.4
XLogP	6.7
Topological Polar Surface Area	37.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	13
Heavy Atom Count	20
Formal Charge	0
Complexity	301

SMILES

CCCCC/C=C\C=C\C=C/CCCCCCC(=O)O

InChI

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-

InChIKey

DQGMPXYVZZCNDQ-KDQYYBQISA-N

Chemical Structure

2D Structure

CAS: 28872-28-8

CID: 5282817

Formula: C18H30O2

MW: 278.4

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	278.4
XLogP3	6.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	13
Exact Mass	278.224580195
Monoisotopic Mass	278.224580195
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	301
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Alternative Products

Catalog	Name
452831-01	Jacaric Acid
GTR19263071-01	Jacaric acid methyl ester
TRC-J210380-10MG	Jacaric Acid (10mg/mL in Ethanol)
OR1071368-01	Acid-apeg6-acid
MBS6083807-01	Medronic Acid (Methylenebiphosphonic Acid, Methylenediphosphonic Acid, Methanebisphosphonic Acid, Methanediphosphonic Acid, MDP)
L2500-01	Lipoic Acid (Thioctic Acid, (±) -α-Lipoic Acid)
041005	Cacodylic Acid (dimethylarsonic acid, dimethylarsinic acid)
MBS641082-01	Lipoic Acid (Thioctic Acid, Alpha Lipoic Acid)
275335-01	Ethylenediaminediacetic acid dipropionic acid
O8099-01	Oxalacetic Acid (Oxaloacetic acid)

Jacaric Acid

Chemical Information

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