Structure Database (LMSD)

Common Name
(Z)-3-(pentadec-8-en-1-yl)phenol
Systematic Name
(Z)-3-(pentadec-8-en-1-yl)phenol
Synonyms
LM ID
LMPK15010007
Formula
C21H34O
Exact Mass
Calculate m/z
302.260966
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Phenolic lipids [PK15]
Alkyl phenols and derivatives [PK1501]

Biological Context

Cardanol monoene is a phenol found in cashew nut shell liquid that reversibly inhibits tyrosinase with an IC50 value of 56 µM in vitro.1 It halts the cell cycle at the S phase and inhibits proliferation dose- and time-dependently in M14 melanoma cells (IC50s = 23.15 and 12.30 µM after 24 and 48 hours of treatment, respectively).2 Cardanol monoene also induces apoptosis via the intrinsic pathway following the accumulation of reactive oxygen species (ROS). A mixture of cardanol mono-, di-, and triene is used to synthesize cardanol-metal complexes that inhibit uropathogenic E. coli biofilm formation.3

This information has been provided by Cayman Chemical

References

1. Su, W.-C., Lin, Y.-F., Wang, Y.-X., et al. Mitochondria-associated apoptosis in human melanoma cells induced by cardanol monoene from cashew nut shell liquid. J. Agric. Food Chem. 65(28), 5620-5631 (2017).
2. Yu, X.-P., Su, W.-C., Wang, Q., et al. Inhibitory mechanism of cardanols on tyrosinase. Proc. Biochem. 51(12), 223-2237 (2016).
3. Lalitha, K., Sandeep, M., Prasad, Y.S., et al. Intrinsic hydrophobic antibacterial thin film from renewable resources: Application in the development of anti-biofilm urinary catheters. ACS Sus. Chem. Eng. (Univ. of Berlin) 5(1), 436-449 (2017).

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)
YLKVIMNNMLKUGJ-FPLPWBNLSA-N
InChi (Click to copy)
InChI=1S/C21H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-20-17-15-18-21(22)19-20/h7-8,15,17-19,22H,2-6,9-14,16H2,1H3/b8-7-
SMILES (Click to copy)
C1C=C(CCCCCCC/C=C\CCCCCC)C=C(O)C=1

Other Databases

KEGG ID
C10785
PubChem CID
5281854
Cayman ID
23154

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 1
Aromatic Rings 1
Rotatable Bonds 13
Van der Waals Molecular Volume 346.83
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 6.80
Molar Refractivity 97.41

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Created at
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Updated at
10th Mar 2024