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Cardanol (C15:1)

CAS# 501-26-8

Cardanol (C15:1)

2D Structure

Catalog No. BCN3751----Order now to get a substantial discount!

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3D structure

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Cardanol (C15:1)

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Chemical Properties of Cardanol (C15:1)

Cas No. 501-26-8 SDF Download SDF
PubChem ID 5281854 Appearance Powder
Formula C21H34O M.Wt 302.3
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-[(Z)-pentadec-8-enyl]phenol
SMILES CCCCCCC=CCCCCCCCC1=CC(=CC=C1)O
Standard InChIKey YLKVIMNNMLKUGJ-FPLPWBNLSA-N
Standard InChI 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-
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Cardanol (C15:1)

The fruit of Ginkgo biloba

Biological Activity of Cardanol (C15:1)

DescriptionCardanol (C15:1) possesses the same side chain as anacardic acid (C15:1), acted neither as a substrate nor as an inhibitor of lipoxygenase-1.
In vitro

Lipoxygenase inhibitory activity of anacardic acids.[Pubmed: 15913294 ]

J Agric Food Chem. 2005 Jun 1;53(11):4350-4.


METHODS AND RESULTS:
6[8'(Z)-pentadecenyl]salicylic acid, otherwise known as anacardic acid (C15:1), inhibited the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) with an IC50 of 6.8 microM. The inhibition of the enzyme by anacardic acid (C15:1) is a slow and reversible reaction without residual activity. The inhibition kinetics analyzed by Dixon plots indicates that anacardic acid (C15:1) is a competitive inhibitor and the inhibition constant, KI, was obtained as 2.8 microM. Although anacardic acid (C15:1) inhibited the linoleic acid peroxidation without being oxidized, 6[8'(Z),11'(Z)-pentadecadienyl]salicylic acid, otherwise known as anacardic acid (C15:2), was dioxygenated at low concentrations as a substrate. In addition, anacardic acid (C15:2) was also found to exhibit time-dependent inhibition of lipoxygenase-1.
CONCLUSIONS:
The alk(en)yl side chain of anacardic acids is essential to elicit the inhibitory activity. However, the hydrophobic interaction alone is not enough because Cardanol (C15:1), which possesses the same side chain as anacardic acid (C15:1), acted neither as a substrate nor as an inhibitor.

Protocol of Cardanol (C15:1)

Structure Identification
Journal of the Science of Food & Agriculture, 2010 , 52 (1) :71-83.

Long chain phenols--the thermal and oxidative deterioration of phenolic lipids from the cashew (Anacardium occidentale) nut shell.[Reference: WebLink]


METHODS AND RESULTS:
The thermal and oxidative deterioration of a mixture comprising the (15:0)-, (15:1)-, (15:2)- and (15:3)-cardanols has been investigated by HPLC analysis. In air the oxidative deterioration is dependent on reaction time, unsaturated structure and temperature, being significant at 180 degrees C and fairly extensive at 240 degrees C. The reactivity of the constituents follows the sequence cardanol (15:3) > cardanol (15:2) > cardanol (15:1) (Cardanol (C15:1) )> (cardanol-3-pentadecylphenol) (15:0). At 180 degrees C, replacement of the aerial atmosphere by nitrogen retards the deterioration although in the upper range an inert atmosphere has only a marginal effect. The mixture and the individual cardanol constituents behave similarly. The results are relevant to distillation procedures for purifying cardanol, to other unsaturated lipid systems and to the technical processing of the product known as technical cashew nut-shell liquid from the cashew nut Anacardium occidentale L.
CONCLUSIONS:
Rate studies indicate that first order kinetics prevail in a nitrogen atmosphere. In air a second order rate of reaction was not always observed.

Cardanol (C15:1) Dilution Calculator

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Cardanol (C15:1) Molarity Calculator

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Preparing Stock Solutions of Cardanol (C15:1)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.308 mL 16.5399 mL 33.0797 mL 66.1594 mL 82.6993 mL
5 mM 0.6616 mL 3.308 mL 6.6159 mL 13.2319 mL 16.5399 mL
10 mM 0.3308 mL 1.654 mL 3.308 mL 6.6159 mL 8.2699 mL
50 mM 0.0662 mL 0.3308 mL 0.6616 mL 1.3232 mL 1.654 mL
100 mM 0.0331 mL 0.1654 mL 0.3308 mL 0.6616 mL 0.827 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Cardanol (C15:1)

Lipoxygenase inhibitory activity of anacardic acids.[Pubmed:15913294]

J Agric Food Chem. 2005 Jun 1;53(11):4350-4.

6[8'(Z)-pentadecenyl]salicylic acid, otherwise known as anacardic acid (C15:1), inhibited the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) with an IC50 of 6.8 microM. The inhibition of the enzyme by anacardic acid (C15:1) is a slow and reversible reaction without residual activity. The inhibition kinetics analyzed by Dixon plots indicates that anacardic acid (C15:1) is a competitive inhibitor and the inhibition constant, KI, was obtained as 2.8 microM. Although anacardic acid (C15:1) inhibited the linoleic acid peroxidation without being oxidized, 6[8'(Z),11'(Z)-pentadecadienyl]salicylic acid, otherwise known as anacardic acid (C15:2), was dioxygenated at low concentrations as a substrate. In addition, anacardic acid (C15:2) was also found to exhibit time-dependent inhibition of lipoxygenase-1. The alk(en)yl side chain of anacardic acids is essential to elicit the inhibitory activity. However, the hydrophobic interaction alone is not enough because Cardanol (C15:1), which possesses the same side chain as anacardic acid (C15:1), acted neither as a substrate nor as an inhibitor.

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