Cardanol diene | CAS# 51546-63-5 | inhibits tyrosinase

MedKoo Cat#: 412341 | Name: Cardanol diene

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cardanol diene is a phenol found in cashew nut shell liquid that inhibits tyrosinase with an IC50 value of 52.5 μM in vitro. Cardanol diene is also used to synthesize cardanol-metal complexes that inhibit uropathogenic E. coli biofilm formation.

Chemical Structure

Cardanol diene

CAS#51546-63-5

Theoretical Analysis

MedKoo Cat#: 412341

Name: Cardanol diene

CAS#: 51546-63-5

Chemical Formula: C21H32O

Exact Mass: 300.2453

Molecular Weight: 300.49

Elemental Analysis: C, 83.94; H, 10.73; O, 5.32

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks
5mg	USD 1,250.00	2 Weeks

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Related CAS #

No Data

Synonym

Cardanol diene; UNIIR5UNJ6B02F; UNII R5UNJ6B02F; UNII-R5UNJ6B02F

IUPAC/Chemical Name

Phenol, 3-(8,11-pentadecadienyl)-, (Z,Z)-

InChi Key

FAYVLNWNMNHXGA-UTOQUPLUSA-N

InChi Code

InChI=1S/C21H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-20-17-15-18-21(22)19-20/h4-5,7-8,15,17-19,22H,2-3,6,9-14,16H2,1H3/b5-4-,8-7-

SMILES Code

OC1=CC=CC(CCCCCCC/C=C\C/C=C\CCC)=C1

Appearance

Oil

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 300.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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PMID: 36365690; PMCID: PMC9658813. 5: Sunny LP, Srikanth P, Sunitha AK, Tembulkar N, Abraham JN. Tryptophan- cardanol fluorescent nanoparticles inhibit α-synuclein aggregation and disrupt amyloid fibrils. J Pept Sci. 2022 Apr;28(4):e3374. doi: 10.1002/psc.3374. Epub 2021 Oct 14. PMID: 34651357. 6: Schneider BU, Meza A, Beatriz A, Pesarini JR, Carvalho PC, Mauro Mde O, Karaziack CB, Cunha-Laura AL, Monreal AC, Matuo R, Lima DP, Oliveira RJ. Cardanol: toxicogenetic assessment and its effects when combined with cyclophosphamide. Genet Mol Biol. 2016 Apr-Jun;39(2):279-89. doi: 10.1590/1678-4685-GMB-2015-0170. PMID: 27303909; PMCID: PMC4910563. 7: Moreira MM, Farrapo MT, Sousa Pereira RC, Rocha da Silva LR, Koller G, Watson T, Feitosa VP, Lomonaco D. Methacrylic monomer derived from cardanol incorporated in dental adhesive as a polymerizable collagen crosslinker. Dent Mater. 2022 Oct;38(10):1610-1622. doi: 10.1016/j.dental.2022.08.008. Epub 2022 Aug 29. PMID: 36050192. 8: Kinaci E, Can E, Scala JJ, Palmese GR. Epoxidation of Cardanol's Terminal Double Bond. Polymers (Basel). 2020 Sep 16;12(9):2104. doi: 10.3390/polym12092104. PMID: 32947830; PMCID: PMC7570343. 9: Manarin E, Corsini F, Trano S, Fagiolari L, Amici J, Francia C, Bodoardo S, Turri S, Bella F, Griffini G. Cardanol-Derived Epoxy Resins as Biobased Gel Polymer Electrolytes for Potassium-Ion Conduction. ACS Appl Polym Mater. 2022 May 13;4(5):3855-3865. doi: 10.1021/acsapm.2c00335. Epub 2022 Apr 29. PMID: 35601462; PMCID: PMC9112699. 10: Kinaci E, Can E, Scala JJ, Palmese GR. Influence of Epoxidized Cardanol Functionality and Reactivity on Network Formation and Properties. Polymers (Basel). 2020 Aug 29;12(9):1956. doi: 10.3390/polym12091956. PMID: 32872398; PMCID: PMC7563135. 11: Faria DL, Scatolino MV, de Oliveira JE, Gonçalves FG, Soriano J, de Paula Protásio T, Lelis RCC, de Carvalho LMH, Mendes LM, Junior JBG. Cardanol-based adhesive with reduced formaldehyde emission to produce particleboards with waste from bean crops. Environ Sci Pollut Res Int. 2023 Apr;30(16):48270-48287. doi: 10.1007/s11356-023-25764-5. Epub 2023 Feb 9. PMID: 36759406. 12: Chen X, Zhang X, Chen J, Bai W, Zheng X, Lin Q, Lin F, Xu Y. Two-dimensional lamellar polyimide/cardanol-based benzoxazine copper polymer composite coatings with excellent anti-corrosion performance. RSC Adv. 2022 Apr 7;12(17):10766-10777. doi: 10.1039/d1ra08844k. PMID: 35425021; PMCID: PMC8988169. 13: Luo Y, Liang W, Ma W, Wang P, Zhu T, Xue S, Yuan Z, Gao H, Chen Y, Wang Y. Cardanol-derived cationic surfactants enabling the superior antibacterial activity of single-walled carbon nanotubes. Nanotechnology. 2020 Apr 9;31(26):265603. doi: 10.1088/1361-6528/ab7aa4. Epub 2020 Feb 27. PMID: 32106102. 14: Zheng Y, Chen L, Wang X, Wu G. Modification of Renewable Cardanol onto Carbon Fiber for the Improved Interfacial Properties of Advanced Polymer Composites. Polymers (Basel). 2019 Dec 28;12(1):45. doi: 10.3390/polym12010045. PMID: 31905612; PMCID: PMC7023525. 15: Zeng L, Jiang L, Yao X, Wang T, Shi B, Lei F. [Preparation and chromatographic performance of cardanol-bonded silica stationary phase]. Se Pu. 2022 Jun;40(6):547-555. Chinese. doi: 10.3724/SP.J.1123.2021.12023. PMID: 35616200; PMCID: PMC9404126. 16: Jia P, Zhang M, Hu L, Wang R, Sun C, Zhou Y. Cardanol Groups Grafted on Poly(vinyl chloride)-Synthesis, Performance and Plasticization Mechanism. Polymers (Basel). 2017 Nov 15;9(11):621. doi: 10.3390/polym9110621. PMID: 30965920; PMCID: PMC6418606. 17: Buahorm S, Puthong S, Palaga T, Lirdprapamongkol K, Phuwapraisirisan P, Svasti J, Chanchao C. Cardanol isolated from Thai Apis mellifera propolis induces cell cycle arrest and apoptosis of BT-474 breast cancer cells via p21 upregulation. Daru. 2015 Dec 22;23:55. doi: 10.1186/s40199-015-0138-1. PMID: 26694491; PMCID: PMC4687141. 18: Sang M, Meng Y, Wang S, Long Z. Graphene/cardanol modified phenolic resin for the development of carbon fiber paper-based composites. RSC Adv. 2018 Jul 6;8(43):24464-24469. doi: 10.1039/c8ra02699h. PMID: 35539179; PMCID: PMC9082169. 19: Denis M, Le Borgne D, Sonnier R, Caillol S, Totee C, Negrell C. Phosphorus Modified Cardanol: A Greener Route to Reduce VolaTile Organic Compounds and Impart Flame Retardant Properties to Alkyd Resin Coatings. Molecules. 2022 Jul 30;27(15):4880. doi: 10.3390/molecules27154880. PMID: 35956832; PMCID: PMC9369946. 20: Appavoo D, Amarnath N, Lochab B. Cardanol and Eugenol Sourced Sustainable Non-halogen Flame Retardants for Enhanced Stability of Renewable Polybenzoxazines. Front Chem. 2020 Sep 30;8:711. doi: 10.3389/fchem.2020.00711. PMID: 33195009; PMCID: PMC7554585.