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Jacaric acid

CAT: 0804-HY-121619-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-121619-02Size:5 mg
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Description
Jacaric acid is a conjugated linolenic acid, which inhibits viability in cells PC-3 (IC50 is 11.8 μM), LNCaP (IC50 is 2.2 μM) and DLD-1, induces apoptosis and necrosis[1]. Jacaric acid exhibits anticaner activity against prostate cancer and adenocarcinoma[2]. Jacaric acid exhibits immunomodulating activity in murine peritoneal macrophages as an immunopotentiator[3]. Jacaric acid is orally active.
CAS Number
28872-28-8
UNSPSC
12352211
Hazard Statement
H225-H350
Target
Apoptosis
Type
Natural Products
Related Pathways
Apoptosis
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/jacaric-acid.html
Solubility
10 mM in DMSO
Smiles
CCCCC/C=C\C=C\C=C/CCCCCCC(O)=O
Molecular Formula
C18H30O2
Molecular Weight
278.43
Precautions
P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P405-P501
References & Citations
[1]Gasmi J, et al., Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure-activity study. Phytomedicine. 2013 Jun 15;20 (8-9) :734-42..|[2]Shinohara N, et al., Jacaric acid, a linolenic acid isomer with a conjugated triene system, has a strong antitumor effect in vitro and in vivo. Biochim Biophys Acta. 2012 Jul;1821 (7) :980-8.|[3]Liu WN, et al., The Immunomodulatory Activity of Jacaric Acid, a Conjugated Linolenic Acid Isomer, on Murine Peritoneal Macrophages. PLoS One. 2015 Dec 2;10 (12) :e0143684.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Jacaric acid

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

CAS Number28872-28-8
PubChem CID5282817
IUPAC Name(8Z,10E,12Z)-octadeca-8,10,12-trienoic acid
Molecular FormulaC18H30O2
Molecular Weight278.4
XLogP6.7
Topological Polar Surface Area37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count13
Heavy Atom Count20
Formal Charge0
Complexity301
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
2D structure of Jacaric acid
CAS: 28872-28-8
CID: 5282817
Formula: C18H30O2
MW: 278.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight278.4
XLogP36.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count13
Exact Mass278.224580195
Monoisotopic Mass278.224580195
Topological Polar Surface Area37.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity301
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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