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

Hodoodo CAT#: H526558

CAS#: 16611-84-0

Description: Anacardic acid is an anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial agent, inhibiting the histone acetyltransferase (HAT) activity of the transcription co-activators p300 and p300/CREB-binding protein-associated factor (pCAF), also inhibiting NF-kappaB activation, IkappaB-a phosphorylation, and prohibiting p65 nuclear translocation.

Chemical Structure

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Anacardic acid
CAS# 16611-84-0
Instruction

Theoretical Analysis

Hodoodo Cat#: H526558
Name: Anacardic acid
CAS#: 16611-84-0
Chemical Formula: C22H36O3
Exact Mass: 348.27
Molecular Weight: 348.527
Elemental Analysis: C, 75.82; H, 10.41; O, 13.77

Price and Availability

Size Price Availability Quantity
1mg USD 170 2 Weeks
5mg USD 300 2 Weeks
10mg USD 550 2 Weeks
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Synonym: Anacardic acid

IUPAC/Chemical Name: 2-Hydroxy-6-pentadecyl-benzoic acid

InChi Key: ADFWQBGTDJIESE-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h15,17-18,23H,2-14,16H2,1H3,(H,24,25)

SMILES Code: O=C(O)C1=C(CCCCCCCCCCCCCCC)C=CC=C1O

Appearance: Solid powder

Purity: >98% (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: >2 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 348.53 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: da Silva DPB, Florentino IF, da Silva Moreira LK, Brito AF, Carvalho VV, Rodrigues MF, Vasconcelos GA, Vaz BG, Pereira-Junior MA, Fernandes KF, Costa EA. Chemical characterization and pharmacological assessment of polysaccharide free, standardized cashew gum extract (Anacardium occidentale L.). J Ethnopharmacol. 2017 Nov 21;213:395-402. doi: 10.1016/j.jep.2017.11.021. [Epub ahead of print] PubMed PMID: 29166575.

2: Guo Z, Zhang Z, Wang Q, Zhang J, Wang L, Zhang Q, Li H, Wu S. Manganese chloride induces histone acetylation changes in neuronal cells: Its role in manganese-induced damage. Neurotoxicology. 2017 Nov 16. pii: S0161-813X(17)30226-7. doi: 10.1016/j.neuro.2017.11.003. [Epub ahead of print] PubMed PMID: 29155171.

3: Kim MK, Kim EJ, Kim JE, Lee DH, Chung JH. Anacardic acid reduces lipogenesis in human differentiated adipocytes via inhibition of histone acetylation. J Dermatol Sci. 2017 Oct 18. pii: S0923-1811(17)30057-9. doi: 10.1016/j.jdermsci.2017.10.004. [Epub ahead of print] PubMed PMID: 29111182.

4: Zhang Z, Guo Z, Zhan Y, Li H, Wu S. Role of histone acetylation in activation of nuclear factor erythroid 2-related factor 2/heme oxygenase 1 pathway by manganese chloride. Toxicol Appl Pharmacol. 2017 Dec 1;336:94-100. doi: 10.1016/j.taap.2017.10.011. Epub 2017 Oct 17. PubMed PMID: 29054681.

5: Mattison CP, Malveira Cavalcante J, Izabel Gallão M, Sousa de Brito E. Effects of industrial cashew nut processing on anacardic acid content and allergen recognition by IgE. Food Chem. 2018 Feb 1;240:370-376. doi: 10.1016/j.foodchem.2017.07.146. Epub 2017 Jul 27. PubMed PMID: 28946285.

6: M Ashraf S, Rathinasamy K. Antibacterial and anticancer activity of the purified cashew nut shell liquid: implications in cancer chemotherapy and wound healing. Nat Prod Res. 2017 Sep 21:1-5. doi: 10.1080/14786419.2017.1380022. [Epub ahead of print] PubMed PMID: 28934859.

7: Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY. Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. PubMed PMID: 28923537; PubMed Central PMCID: PMC5602478.

8: Schultz DJ, Muluhngwi P, Alizadeh-Rad N, Green MA, Rouchka EC, Waigel SJ, Klinge CM. Genome-wide miRNA response to anacardic acid in breast cancer cells. PLoS One. 2017 Sep 8;12(9):e0184471. doi: 10.1371/journal.pone.0184471. eCollection 2017. PubMed PMID: 28886127; PubMed Central PMCID: PMC5590942.

9: Prinsloo G, Marokane CK, Street RA. Anti-HIV activity of southern African plants: Current developments, phytochemistry and future research. J Ethnopharmacol. 2018 Jan 10;210:133-155. doi: 10.1016/j.jep.2017.08.005. Epub 2017 Aug 12. Review. PubMed PMID: 28807850.

10: Tan J, Jiang X, Yin G, He L, Liu J, Long Z, Jiang Z, Yao K. Anacardic acid induces cell apoptosis of prostatic cancer through autophagy by ER stress/DAPK3/Akt signaling pathway. Oncol Rep. 2017 Sep;38(3):1373-1382. doi: 10.3892/or.2017.5841. Epub 2017 Jul 20. PubMed PMID: 28731173; PubMed Central PMCID: PMC5549027.

11: Fernandez HR, Lindén SK. The aspirin metabolite salicylate inhibits lysine acetyltransferases and MUC1 induced epithelial to mesenchymal transition. Sci Rep. 2017 Jul 17;7(1):5626. doi: 10.1038/s41598-017-06149-4. PubMed PMID: 28717171; PubMed Central PMCID: PMC5514058.

12: Choi JH, Jeong YJ, Yu AR, Yoon KS, Choe W, Ha J, Kim SS, Yeo EJ, Kang I. Fluoxetine induces apoptosis through endoplasmic reticulum stress via mitogen-activated protein kinase activation and histone hyperacetylation in SK-N-BE(2)-M17 human neuroblastoma cells. Apoptosis. 2017 Sep;22(9):1079-1097. doi: 10.1007/s10495-017-1390-2. PubMed PMID: 28647884.

13: Nanni S, Re A, Ripoli C, Gowran A, Nigro P, D'Amario D, Amodeo A, Crea F, Grassi C, Pontecorvi A, Farsetti A, Colussi C. The nuclear pore protein Nup153 associates with chromatin and regulates cardiac gene expression in dystrophic mdx hearts. Cardiovasc Res. 2016 Nov 1;112(2):555-567. doi: 10.1093/cvr/cvw204. PubMed PMID: 28513807.

14: Moradi-Afrapoli F, van der Merwe H, De Mieri M, Wilhelm A, Stadler M, Zietsman PC, Hering S, Swart K, Hamburger M. HPLC-Based Activity Profiling for GABAA Receptor Modulators in Searsia pyroides Using a Larval Zebrafish Locomotor Assay. Planta Med. 2017 Oct;83(14-15):1169-1175. doi: 10.1055/s-0043-110768. Epub 2017 May 16. PubMed PMID: 28511229.

15: Kim MK, Shin MH, Kim YK, Kim HY, Lee YR, Lee DH, Chung JH. Anacardic acid ameliorates ultraviolet irradiation-induced damage to human skin. J Dermatol Sci. 2017 Jun;86(3):252-255. doi: 10.1016/j.jdermsci.2017.03.019. Epub 2017 Mar 30. PubMed PMID: 28404454.

16: Morais SM, Silva KA, Araujo H, Vieira IG, Alves DR, Fontenelle RO, Silva AM. Anacardic Acid Constituents from Cashew Nut Shell Liquid: NMR Characterization and the Effect of Unsaturation on Its Biological Activities. Pharmaceuticals (Basel). 2017 Mar 16;10(1). pii: E31. doi: 10.3390/ph10010031. PubMed PMID: 28300791; PubMed Central PMCID: PMC5374435.

17: Braz NM, Freitas ER, Trevisan MT, do Nascimento GA, Salles RP, Cruz CE, Farias NN, da Silva IN, Watanabe PH. Serum biochemical profile, enzymatic activity and lipid peroxidation in organs of laying hens fed diets containing cashew nut shell liquid. J Anim Physiol Anim Nutr (Berl). 2017 Mar 16. doi: 10.1111/jpn.12659. [Epub ahead of print] PubMed PMID: 28299816.

18: Cunha AG, Brito ES, Moura CF, Ribeiro PR, Miranda MR. UPLC-qTOF-MS/MS-based phenolic profile and their biosynthetic enzyme activity used to discriminate between cashew apple (Anacardium occidentale L.) maturation stages. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Apr 15;1051:24-32. doi: 10.1016/j.jchromb.2017.02.022. Epub 2017 Feb 21. PubMed PMID: 28285020.

19: Yang F, Zhou S, Wang C, Huang Y, Li H, Wang Y, Zhu Z, Tang J, Yan M. Epigenetic modifications of interleukin-6 in synovial fibroblasts from osteoarthritis patients. Sci Rep. 2017 Mar 6;7:43592. doi: 10.1038/srep43592. PubMed PMID: 28262826; PubMed Central PMCID: PMC5337936.

20: Kim MK, Kim EJ, Cheng Y, Shin MH, Oh JH, Lee DH, Chung JH. Inhibition of DNA Methylation in the COL1A2 Promoter by Anacardic Acid Prevents UV-Induced Decrease of Type I Procollagen Expression. J Invest Dermatol. 2017 Jun;137(6):1343-1352. doi: 10.1016/j.jid.2017.02.005. Epub 2017 Feb 24. PubMed PMID: 28237615.