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499-44-5 | Hinokitiol
CAS No: 499-44-5 Catalog No: AG003QXP MDL No:MFCD00059582
Product Description
Catalog Number:
AG003QXP
Chemical Name:
Hinokitiol
CAS Number:
499-44-5
Molecular Formula:
C10H12O2
Molecular Weight:
164.2011
MDL Number:
MFCD00059582
IUPAC Name:
2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
InChI:
InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
InChI Key:
FUWUEFKEXZQKKA-UHFFFAOYSA-N
SMILES:
CC(c1cccc(=O)c(c1)O)C
EC Number:
207-880-7
UNII:
U5335D6EBI
NSC Number:
18804
Properties
Complexity:
280
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
164.084g/mol
Formal Charge:
0
Heavy Atom Count:
12
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
164.204g/mol
Monoisotopic Mass:
164.084g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
37.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.1
Literature
| Title | Journal |
|---|---|
| Hinokitiol induces autophagy in murine breast and colorectal cancer cells. | Environmental toxicology 20160101 |
| Tropolones as lead-like natural products: the development of potent and selective histone deacetylase inhibitors. | ACS medicinal chemistry letters 20130808 |
| The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs. | Organic & biomolecular chemistry 20121121 |
| Synthesis and electrochemistry of organometallic cobaltadithiaazulenes. | Inorganic chemistry 20121015 |
| In vitro and in vivo anti-plasmodial activity of essential oils, including hinokitiol. | The Southeast Asian journal of tropical medicine and public health 20120301 |
| Topical hypopigmenting agents for pigmentary disorders and their mechanisms of action. | Annals of dermatology 20120201 |
| Effects of a combination of hinokitiol (β-thujaplicin) and an organic acid mixture on ruminal fermentation in heifers fed a high-grain diet. | Animal science journal = Nihon chikusan Gakkaiho 20120101 |
| Preventive effects of β-thujaplicin against UVB-induced MMP-1 and MMP-3 mRNA expressions in skin fibroblasts. | The American journal of Chinese medicine 20120101 |
| In vitro and in vivo therapeutics of β-thujaplicin on LPS-induced inflammation in macrophages and septic shock in mice. | International journal of immunopathology and pharmacology 20120101 |
| A 13-week subchronic toxicity study of hinokitiol administered in the diet to F344 rats. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110801 |
| trans-Bis(hinokitiolato)copper(II) trans-bis(hinokitiolato)palladium(II) cocrystals with (5/1) and (3/2) formulations. | Acta crystallographica. Section C, Crystal structure communications 20110401 |
| Identifying chelators for metalloprotein inhibitors using a fragment-based approach. | Journal of medicinal chemistry 20110127 |
| The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease. | International journal of molecular sciences 20110101 |
| Cytoplasmic Skp2 expression is increased in human melanoma and correlated with patient survival. | PloS one 20110101 |
| Bioactivity of miltefosine against aquatic stages of Schistosoma mansoni, Schistosoma haematobium and their snail hosts, supported by scanning electron microscopy. | Parasites & vectors 20110101 |
| Effect of oral care gel on the quality of life for oral lichen planus in patients with chronic HCV infection. | Virology journal 20110101 |
| Inhibitory effects of hinokitiol on tyrosinase activity and melanin biosynthesis and its antimicrobial activities. | Journal of enzyme inhibition and medicinal chemistry 20101201 |
| Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins. | Bioorganic & medicinal chemistry 20101115 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Zn(2+) inhibits coronavirus and arterivirus RNA polymerase activity in vitro and zinc ionophores block the replication of these viruses in cell culture. | PLoS pathogens 20101101 |
| catena-Poly[(μ(3)-2-hy-droxy-4-isopropyl-cyclo-hepta-2,4,6-trien-1-onato)(μ(2)-2-hy-droxy-4-isopropyl-cyclo-hepta-2,4,6-trien-1-onato)lead(II)]. | Acta crystallographica. Section E, Structure reports online 20101101 |
| A urea adduct of bis(hinokitiolato)copper(II). | Acta crystallographica. Section C, Crystal structure communications 20101001 |
| Bis(hinokitiolato)copper(II): modification (III). | Acta crystallographica. Section C, Crystal structure communications 20100601 |
| Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases. | Biochemical and biophysical research communications 20100528 |
| Non-classical anticancer agents: synthesis and biological evaluation of zinc(II) heteroleptic complexes. | Dalton transactions (Cambridge, England : 2003) 20100507 |
| In vitro skin permeation of hinokitiol loaded in vesicles composed of behenyltrimethylammonium chloride and stearic acid. | Drug development and industrial pharmacy 20100501 |
| Time-kill assay results for a linalool-hinokitiol-based eyelid cleanser for lid hygiene. | Cornea 20100501 |
| Synthesis of tropolone derivatives and evaluation of their in vitro neuroprotective activity. | European journal of medicinal chemistry 20100301 |
| Zinc-dependent effects of small molecules on the insulin-sensitive transcription factor FOXO1a and gluconeogenic genes. | Metallomics : integrated biometal science 20100301 |
| Chemical genetics approach to restoring p27Kip1 reveals novel compounds with antiproliferative activity in prostate cancer cells. | BMC biology 20100101 |
| p27-Associated G1 arrest induced by hinokitiol in human malignant melanoma cells is mediated via down-regulation of pRb, Skp2 ubiquitin ligase, and impairment of Cdk2 function. | Cancer letters 20091228 |
| Antimicrobial activity of fullerenes and their hydroxylated derivatives. | Biocontrol science 20090601 |
| Volatile and non-volatile monoterpenes produced by elicitor-stimulated Cupressus lusitanica cultured cells. | Journal of plant physiology 20090501 |
| High-performance liquid chromatography with dual-wavelength ultraviolet detection for measurement of hinokitiol in personal care products. | Journal of cosmetic science 20090101 |
| Harnessing gene expression to identify the genetic basis of drug resistance. | Molecular systems biology 20090101 |
| High production of beta-thujaplicin glycosides by immobilized plant cells of Nicotiana tabacum. | Acta biologica Hungarica 20080901 |
| In vivo hair growth promotion effects of cosmetic preparations containing hinokitiol-loaded poly(epsilon-caprolacton) nanocapsules. | Journal of microencapsulation 20080801 |
| Antifungal properties of ethanolic extract and its active compounds from Calocedrus macrolepis var. formosana (Florin) heartwood. | Bioresource technology 20080701 |
| Hinokitiol, a natural tropolone derivative, inhibits TNF-alpha production in LPS-activated macrophages via suppression of NF-kappaB. | Planta medica 20080601 |
| Antifungal mechanism of hinokitiol against Candida albicans. | Biological & pharmaceutical bulletin 20080401 |
| In vitro permeation study of hinokitiol: effects of vehicles and enhancers. | Drug delivery 20080101 |
| The mechanism of the bactericidal activity of hinokitiol. | Biocontrol science 20070901 |
| Growth inhibitory effect of shelf life extending agents on Bacillus subtilis IAM 1026. | Biocontrol science 20070601 |
| UV-visible and 1H or 13C NMR spectroscopic studies on the specific interaction between lithium ions and the anion from tropolone or 4-isopropyltropolone (hinokitiol) and on the formation of protonated tropolones in acetonitrile or other solvents. | The journal of physical chemistry. B 20070222 |
| Baicalein induction of hydroxyl radical formation via 12-lipoxygenase in human platelets: an ESR study. | Journal of agricultural and food chemistry 20070207 |
| Reactive oxygen species, nitric oxide, and their interactions play different roles in Cupressus lusitanica cell death and phytoalexin biosynthesis. | The New phytologist 20070101 |
| Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines. | Biochemical and biophysical research communications 20061208 |
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | Journal of molecular graphics & modelling 20061101 |
| Lack of hinokitiol (beta-thujaplicin) carcinogenicity in F344/DuCrj rats. | The Journal of toxicological sciences 20061001 |
| Differential regulation of melanosomal proteins after hinokitiol treatment. | Journal of dermatological science 20060901 |
| The excellence of Aomori Hiba (Hinokiasunaro) in its use as building materials of Buddhist temples and Shinto shrines. | Biocontrol science 20060601 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Preferential inhibition of the magnesium-dependent strand transfer reaction of HIV-1 integrase by alpha-hydroxytropolones. | Molecular pharmacology 20060401 |
| Therapeutic effects of beta-thujaplicin eardrops on canine Malassezia-related otitis externa. | The Journal of veterinary medical science 20060401 |
| Searching for a new anti-HCV therapy: synthesis and properties of tropolone derivatives. | Biochemical and biophysical research communications 20060310 |
| Signal transduction and metabolic flux of beta-thujaplicin and monoterpene biosynthesis in elicited Cupressus lusitanica cell cultures. | Metabolic engineering 20060101 |
| Human metallothionein gene expression is upregulated by beta-thujaplicin: possible involvement of protein kinase C and reactive oxygen species. | Biological & pharmaceutical bulletin 20060101 |
| Arachidonate 12-lipoxygenases with reference to their selective inhibitors. | Biochemical and biophysical research communications 20051209 |
| Inhibitory effects of 4-n-butylresorcinol on tyrosinase activity and melanin synthesis. | Biological & pharmaceutical bulletin 20051201 |
| Prooxidant action of hinokitiol: hinokitiol-iron dependent generation of reactive oxygen species. | Basic & clinical pharmacology & toxicology 20051201 |
| Effects of beta-thujaplicin on anti-Malassezia pachydermatis remedy for canine otitis externa. | The Journal of veterinary medical science 20051201 |
| Mosquito larvicidal activity of active constituent derived from Chamaecyparis obtusa leaves against 3 mosquito species. | Journal of the American Mosquito Control Association 20051201 |
| Oxidative stress in plant cell culture: a role in production of beta-thujaplicin by Cupresssus lusitanica suspension culture. | Biotechnology and bioengineering 20050605 |
| Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp. | Journal of agricultural and food chemistry 20050323 |
| Fungal diversity from western redcedar fences and their resistance to beta-thujaplicin. | Antonie van Leeuwenhoek 20050201 |
| Selective inhibition of HIV-1 reverse transcriptase-associated ribonuclease H activity by hydroxylated tropolones. | Nucleic acids research 20050101 |
| Interaction of silver nanoparticles with HIV-1. | Journal of nanobiotechnology 20050101 |
| Biological activity of beta-dolabrin, gamma-thujaplicin, and 4-acetyltropolone, hinokitiol-related compounds. | Biological & pharmaceutical bulletin 20041001 |
| Biological activity of alpha-thujaplicin, the isomer of hinokitiol. | Biological & pharmaceutical bulletin 20040601 |
| Rapid accumulation and metabolism of polyphosphoinositol and its possible role in phytoalexin biosynthesis in yeast elicitor-treated Cupressus lusitanica cell cultures. | Planta 20040501 |
| Jasmonate and ethylene signalling and their interaction are integral parts of the elicitor signalling pathway leading to beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures. | Journal of experimental botany 20040501 |
| Beta-thujaplicin: new quantitative CZE method and adsorption to goethite. | Journal of agricultural and food chemistry 20040324 |
| Evaluation of developmental toxicity of beta-thujaplicin (hinokitiol) following oral administration during organogenesis in rats. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040301 |
| (-)-Epigallocatechin-3-gallate and hinokitiol reduce melanin synthesis via decreased MITF production. | Archives of pharmacal research 20040301 |
| Synthesis and structural characterization of silver(I), aluminium(III) and cobalt(II) complexes with 4-isopropyltropolone (hinokitiol) showing noteworthy biological activities. Action of silver(I)-oxygen bonding complexes on the antimicrobial activities. | Journal of inorganic biochemistry 20040101 |
| Transmission electron microscopy of Schistosoma mansoni cercariae treated with hinokitiol (beta-thujaplicin), a compound for potential skin application against cercarial penetration. | The Tohoku journal of experimental medicine 20040101 |
| Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines. | Anticancer research 20040101 |
| [Antimicrobial activity of hinokitiol against Legionella pneumophila]. | Journal of UOEH 20031201 |
| Biological activity of tropolone. | Biological & pharmaceutical bulletin 20031001 |
| Generation of reactive oxygen species from Hinokitiol under near-UV irradiation. | Bioscience, biotechnology, and biochemistry 20030901 |
| Multiple signalling pathways mediate fungal elicitor-induced beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures. | Journal of experimental botany 20030201 |
| Antibacterial effect of beta-thujaplicin on staphylococci isolated from atopic dermatitis: relationship between changes in the number of viable bacterial cells and clinical improvement in an eczematous lesion of atopic dermatitis. | The Journal of antimicrobial chemotherapy 20030101 |
| Biological activity of 4-acetyltropolone, the minor component of Thujopsis dolabrata SIeb. et Zucc. hondai Mak. | Biological & pharmaceutical bulletin 20020801 |
| Feedback regulation of beta-thujaplicin production and formation of its methyl ether in a suspension culture of Cupressus lusitanica. | Phytochemistry 20020701 |
| New lanostanoids, elfvingic acids A-H, from the fruit body of Elfvingia applanata. | Journal of natural products 20020401 |
| Fungicidal activity of beta-thujaplicin analogues. | Pest management science 20010901 |
| Synthesis and structural characterization of tin(II) and zinc(II) derivatives of cyclic alpha-hydroxyketones, including the structures of Sn(maltol)(2), Sn(tropolone)(2), Zn(tropolone)(2), and Zn(hinokitiol)(2). | Inorganic chemistry 20010813 |
| Cytotoxic effects of beta-thujaplicin on rat thymocytes and prevention by the compound in tributyltin-induced thymocyte damage. | Bulletin of environmental contamination and toxicology 20010701 |
| Biological activity of alpha-thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO. | Biological & pharmaceutical bulletin 20010601 |
| Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes. | Bioscience, biotechnology, and biochemistry 20010501 |
| Improved beta-thujaplicin production in Cupressus lusitanica suspension cultures by fungal elicitor and methyl jasmonate. | Applied microbiology and biotechnology 20010401 |
| Cytotoxicity of the hinokitiol-related compounds, gamma-thujaplicin and beta-dolabrin. | Biological & pharmaceutical bulletin 20010301 |
| Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3. | Cell proliferation 19990201 |
| Thujaplicin-copper chelates inhibit replication of human influenza viruses. | Antiviral research 19980801 |
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