Structure Database (LMSD)

Common Name
5-((8Z,11Z)-pentadeca-8,11,14-trien-1-yl)resorcinol
Systematic Name
5-((8Z,11Z)-pentadeca-8,11,14-trien-1-yl)benzene-1,3-diol
Synonyms
LM ID
LMPK15030022
Formula
C21H30O2
Exact Mass
Calculate m/z
314.22458
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Alkyl resorcinols and derivatives [PK1503]

Biological Context

Cardol triene is a phenol found in cashew nut shell liquid that competitively and irreversibly inhibits mushroom tyrosinase (IC50 = 22.5 µM).1,2 It is schistosomicidal, killing 25, 75, and 100% of S. mansoni worms after 24 hours when used at concentrations of 50, 100, or 200 µM, respectively.3 It has been used as a starting material for the synthesis of bis-benzoxazines.4

This information has been provided by Cayman Chemical

References

1. Zhuang, J.-X., Hu, Y.-H., Yang, M.-H., et al. Irreversible competitive inhibitory kinetics of cardol triene on mushroom tyrosinase. J. Agric. Food Chem. 58(24), 12993-12998 (2010).
2. Tyman, J.H., and Kiong, L.S. Long chain phenols: Part XI. Composition of natural cashew nutshell liquid (Anacardium occidentale) from various sources. Lipids 13(8), 525-532 (1978).
3. Attanasi, O.A., Behalo, M.S., Favi, G., et al. Solvent free synthesis of novel mono- and bis-benzoxazines from cashew nut shell liquid components. Curr. Org. Chem. 16(21), 2613-2621 (2012).
4. Alvarenga, T.A., de Oliveira, P.F., de Souza, J.M., et al. Schistosomicidal activity of alkyl-phenols from the cashew Anacardium occidentale against Schistosoma mansoni adult worms. J. Agric. Food Chem. 64(46), 8821-8827 (2016).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Anacardium occidentale (#171929)
Magnoliopsida (#3398)
Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nut shell oil,
J. Agric. Food Chem., 1991

String Representations

InChiKey (Click to copy)
OOXBEOHCOCMKAC-UTOQUPLUSA-N
InChi (Click to copy)
InChI=1S/C21H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h2,4-5,7-8,16-18,22-23H,1,3,6,9-15H2/b5-4-,8-7-
SMILES (Click to copy)
C1(O)C=C(CCCCCCC/C=C\C/C=C\CC=C)C=C(O)C=1

Other Databases

PubChem CID
13259919
Cayman ID
23374

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 1
Rotatable Bonds 12
Van der Waals Molecular Volume 350.34
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 6.06
Molar Refractivity 98.89

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Created at
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Updated at
10th Mar 2024