Home Other Building Blocks 2-Hydroxy-6-pentadecylbenzoic acid

2-Hydroxy-6-pentadecylbenzoic acid

CAS No.:
16611-84-0
Catalog Number:
AG001WI4
Molecular Formula:
C22H36O3
Molecular Weight:
348.5194
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$85
- +
5mg
≥98%
1 week
United States
$110
- +
10mg
≥98%
1 week
United States
$151
- +
25mg
98%
1 week
United States
$279
- +
Product Description
Catalog Number:
AG001WI4
Chemical Name:
2-Hydroxy-6-pentadecylbenzoic acid
CAS Number:
16611-84-0
Molecular Formula:
C22H36O3
Molecular Weight:
348.5194
MDL Number:
MFCD07368254
IUPAC Name:
2-hydroxy-6-pentadecylbenzoic acid
InChI:
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)
InChI Key:
ADFWQBGTDJIESE-UHFFFAOYSA-N
SMILES:
CCCCCCCCCCCCCCCc1cccc(c1C(=O)O)O
EC Number:
234-268-7
Properties
Complexity:
329  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
348.266g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
348.527g/mol
Monoisotopic Mass:
348.266g/mol
Rotatable Bond Count:
15  
Topological Polar Surface Area:
57.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
9.5  
Literature
Title Journal
Role of histone acetylation in activation of nuclear factor erythroid 2-related factor 2/heme oxygenase 1 pathway by manganese chloride. Toxicology and applied pharmacology 20171201
E2 Ubiquitin-conjugating Enzyme, UBE2C Gene, Is Reciprocally Regulated by Wild-type and Gain-of-Function Mutant p53. The Journal of biological chemistry 20160701
The enhancing effect of genistein on apoptosis induced by trichostatin A in lung cancer cells with wild type p53 genes is associated with upregulation of histone acetyltransferase. Toxicology and applied pharmacology 20160201
Small ubiquitin-related modifier-1 modification regulates all-trans-retinoic acid-induced differentiation via stabilization of retinoic acid receptor α. The FEBS journal 20140701
Resveratrol improves cardiomyopathy in dystrophin-deficient mice through SIRT1 protein-mediated modulation of p300 protein. The Journal of biological chemistry 20130222
Environmental alkylphenols modulate cytokine expression in plasmacytoid dendritic cells. PloS one 20130101
Anacardic acid inhibits the catalytic activity of matrix metalloproteinase-2 and matrix metalloproteinase-9. Molecular pharmacology 20121001
Anacardic acid derived salicylates are inhibitors or activators of lipoxygenases. Bioorganic & medicinal chemistry 20120815
Auto-acetylation stabilizes p300 in cardiac myocytes during acute oxidative stress, promoting STAT3 accumulation and cell survival. Breast cancer research and treatment 20120801
Inhibition of PCAF histone acetyltransferase and cytotoxic effect of N-acylanthranilic acids. Archives of pharmacal research 20120801
Probing the effect of intermolecular interaction and understanding the electrostatic moments of anacardic acid in the active site of p300 enzyme via DFT and charge density analysis. Journal of molecular graphics & modelling 20120401
Anacardic acid (6-pentadecylsalicylic acid) inhibits tumor angiogenesis by targeting Src/FAK/Rho GTPases signaling pathway. The Journal of pharmacology and experimental therapeutics 20111101
Effects of Ginkgo biloba constituents on fruit-infesting behavior of codling moth (Cydia pomonella) in apples. Journal of agricultural and food chemistry 20111026
Paraquat induces epigenetic changes by promoting histone acetylation in cell culture models of dopaminergic degeneration. Neurotoxicology 20111001
MRG15 activates the cdc2 promoter via histone acetylation in human cells. Experimental cell research 20110701
SUMO1 negatively regulates reactive oxygen species production from NADPH oxidases. Arteriosclerosis, thrombosis, and vascular biology 20110701
Anacardic acid induces caspase-independent apoptosis and radiosensitizes pituitary adenoma cells. Journal of neurosurgery 20110601
Lunasin-aspirin combination against NIH/3T3 cells transformation induced by chemical carcinogens. Plant foods for human nutrition (Dordrecht, Netherlands) 20110601
Antioxidant, larvicidal and antiacetylcholinesterase activities of cashew nut shell liquid constituents. Acta tropica 20110301
Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells. Clinical epigenetics 20110101
Hydro-ethanolic extract of cashew tree (Anacardium occidentale) nut and its principal compound, anacardic acid, stimulate glucose uptake in C2C12 muscle cells. Molecular nutrition & food research 20101201
New anacardic acid-inspired benzamides: histone lysine acetyltransferase activators. ChemMedChem 20100903
Improved inhibition of the histone acetyltransferase PCAF by an anacardic acid derivative. Bioorganic & medicinal chemistry 20100815
Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids. European journal of medicinal chemistry 20100801
Environmental neurotoxic pesticide increases histone acetylation to promote apoptosis in dopaminergic neuronal cells: relevance to epigenetic mechanisms of neurodegeneration. Molecular pharmacology 20100401
Anacardic acid inhibits estrogen receptor alpha-DNA binding and reduces target gene transcription and breast cancer cell proliferation. Molecular cancer therapeutics 20100301
Histone H4 acetylation is essential to proceed from a histone- to a protamine-based chromatin structure in spermatid nuclei of Drosophila melanogaster. Systems biology in reproductive medicine 20100201
Modulation of cytokine expression in human myeloid dendritic cells by environmental endocrine-disrupting chemicals involves epigenetic regulation. Environmental health perspectives 20100101
Lipoxygenase inhibitory activity of 6-pentadecanylsalicylic acid without prooxidant effect. Natural product communications 20100101
Synergistic induction of endothelin-1 by tumor necrosis factor alpha and interferon gamma is due to enhanced NF-kappaB binding and histone acetylation at specific kappaB sites. The Journal of biological chemistry 20090904
Synthesis of benzamide derivatives of anacardic acid and their cytotoxic activity. European journal of medicinal chemistry 20090601
Enzymatic polymerization of natural anacardic acid and antibiofouling effects of polyanacardic acid coatings. Applied biochemistry and biotechnology 20090501
Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate. Chemistry & biology 20090227
Bisubstrate Inhibitors of the MYST HATs Esa1 and Tip60. Bioorganic & medicinal chemistry 20090201
Isolation of anacardic acid from natural cashew nut shell liquid (CNSL) using supercritical carbon dioxide. Journal of agricultural and food chemistry 20081022
Effects of immature cashew nut-shell liquid (Anacardium occidentale) against oxidative damage in Saccharomyces cerevisiae and inhibition of acetylcholinesterase activity. Genetics and molecular research : GMR 20080909
Synthesis of benzamides related to anacardic acid and their histone acetyltransferase (HAT) inhibitory activities. ChemMedChem 20080901
Histone acetylation and flagellin are essential for Legionella pneumophila-induced cytokine expression. Journal of immunology (Baltimore, Md. : 1950) 20080715
Histone acetyltransferase inhibitor anacardic acid causes changes in global gene expression during in vitro Plasmodium falciparum development. Eukaryotic cell 20080701
Design and evaluation of anacardic acid derivatives as anticavity agents. European journal of medicinal chemistry 20080601
Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-kappaB-regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-kappaBalpha kinase, leading to potentiation of apoptosis. Blood 20080515
Inhibition of HIV-1 protease and RNase H of HIV-1 reverse transcriptase activities by long chain phenols from the sarcotestas of Ginkgo biloba. Planta medica 20080401
Difluoromethylornithine stimulates early cardiac commitment of mesenchymal stem cells in a model of mixed culture with cardiomyocytes. Journal of cellular biochemistry 20080301
Specific small-molecule activator of Aurora kinase A induces autophosphorylation in a cell-free system. Journal of medicinal chemistry 20080227
Preparation of molecularly imprinted polymers using anacardic acid monomers derived from cashew nut shell liquid. Journal of agricultural and food chemistry 20071031
Molecular design of anti-MRSA agents based on the anacardic acid scaffold. Bioorganic & medicinal chemistry 20070915
Characterization of novel inhibitors of histone acetyltransferases. Molecular cancer therapeutics 20070901
Activation of p300 histone acetyltransferase by small molecules altering enzyme structure: probed by surface-enhanced Raman spectroscopy. The journal of physical chemistry. B 20070503
Synthesis of isonicotinoylhydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis. European journal of medicinal chemistry 20070301
Effects of salicylic acid on mushroom tyrosinase and B16 melanoma cells. Zeitschrift fur Naturforschung. C, Journal of biosciences 20070101
Effect of 6-nonadecyl salicylic acid and its methyl ester on the induction of micronuclei in polychromatic erythrocytes in mouse peripheral blood. Mutation research 20061010
Bioactivity of anacardic acid against colorado potato beetle (Leptinotarsa decemlineata) larvae. Journal of agricultural and food chemistry 20061004
Inhibition of histone acetyltransferase activity by anacardic acid sensitizes tumor cells to ionizing radiation. FEBS letters 20060807
Women's health among the Chumash. Evidence-based complementary and alternative medicine : eCAM 20060301
Characterization of alkyl phenols in cashew (Anacardium occidentale) products and assay of their antioxidant capacity. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060201
Lipoxygenase inhibitory activity of anacardic acids. Journal of agricultural and food chemistry 20050601
6-alkylsalicylic acids and 6-alkylresorcylic acids from ants in the genus Crematogaster from Brunei. Journal of chemical ecology 20050201
The transcriptional coactivator p300 plays a critical role in the hypertrophic and protective pathways induced by phenylephrine in cardiac cells but is specific to the hypertrophic effect of urocortin. Chembiochem : a European journal of chemical biology 20050101
Characterization of xanthine oxidase inhibition by anacardic acids. Biochimica et biophysica acta 20040405
Synergistic effects of anacardic acids and methicillin against methicillin resistant Staphylococcus aureus. Bioorganic & medicinal chemistry 20040201
Antibacterial action of anacardic acids against methicillin resistant Staphylococcus aureus (MRSA). Journal of agricultural and food chemistry 20031217
Small molecule modulators of histone acetyltransferase p300. The Journal of biological chemistry 20030523
Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition. Journal of agricultural and food chemistry 20021218
Anacardic acid-mediated changes in membrane potential and pH gradient across liposomal membranes. Biochimica et biophysica acta 20020102
Zoosporicidal activities of anacardic acids against Aphanomyces cochlioides. Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101
Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid. Chemical & pharmaceutical bulletin 20010101
Properties