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499-44-5,MFCD00040180
Catalog No.:AA003QUX

499-44-5 | Hinokitiol

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50mg
99%
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1g
>99.0%(GC)
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5g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003QUX
Chemical Name:
Hinokitiol
CAS Number:
499-44-5
Molecular Formula:
C10H12O2
Molecular Weight:
164.2011
MDL Number:
MFCD00040180
SMILES:
CC(c1cccc(=O)c(c1)O)C
NSC Number:
18804
Properties
Properties
 
BP:
303.4°C at 760 mmHg  
Form:
Solid  
MP:
47-49°C  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
280  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
1  
XLogP3:
2.1  

Downstream Synthesis Route

[1]Sci.Rep.TohokuUniv.,Ser.1:Phys.,Chem.,Astron.,1953,vol.<I>37,p.286,289

[1]ProceedingsoftheJapanAcademy,1952,vol.28,p.192,197    Sci.Rep.TohokuUniv.,Ser.1:Phys.,Chem.,Astron.,1952,vol.<I>36,p.126,147

[1]Sci.Rep.TohokuUniv.,Ser.1:Phys.,Chem.,Astron.,1958,vol.<I>42,p.222,230

[1]Sci.Rep.TohokuUniv.,Ser.1:Phys.,Chem.,Astron.,1958,vol.<I>42,p.222,230

108-31-6    499-44-5   
1-isopropyl-3,4-dioxo-bicyclo3.2.2nonane-6,7-dicarboxylicacid-anhydride 

[1]ProceedingsoftheImperialAcademy(Tokyo),1952,vol.28,p.282,283,284

Literature

Title: Hinokitiol induces autophagy in murine breast and colorectal cancer cells.

Journal: Environmental toxicology 20160101

Title: Tropolones as lead-like natural products: the development of potent and selective histone deacetylase inhibitors.

Journal: ACS medicinal chemistry letters 20130808

Title: The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs.

Journal: Organic & biomolecular chemistry 20121121

Title: Synthesis and electrochemistry of organometallic cobaltadithiaazulenes.

Journal: Inorganic chemistry 20121015

Title: In vitro and in vivo anti-plasmodial activity of essential oils, including hinokitiol.

Journal: The Southeast Asian journal of tropical medicine and public health 20120301

Title: Topical hypopigmenting agents for pigmentary disorders and their mechanisms of action.

Journal: Annals of dermatology 20120201

Title: Effects of a combination of hinokitiol (β-thujaplicin) and an organic acid mixture on ruminal fermentation in heifers fed a high-grain diet.

Journal: Animal science journal = Nihon chikusan Gakkaiho 20120101

Title: Preventive effects of β-thujaplicin against UVB-induced MMP-1 and MMP-3 mRNA expressions in skin fibroblasts.

Journal: The American journal of Chinese medicine 20120101

Title: In vitro and in vivo therapeutics of β-thujaplicin on LPS-induced inflammation in macrophages and septic shock in mice.

Journal: International journal of immunopathology and pharmacology 20120101

Title: A 13-week subchronic toxicity study of hinokitiol administered in the diet to F344 rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110801

Title: trans-Bis(hinokitiolato)copper(II) trans-bis(hinokitiolato)palladium(II) cocrystals with (5/1) and (3/2) formulations.

Journal: Acta crystallographica. Section C, Crystal structure communications 20110401

Title: Identifying chelators for metalloprotein inhibitors using a fragment-based approach.

Journal: Journal of medicinal chemistry 20110127

Title: The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease.

Journal: International journal of molecular sciences 20110101

Title: Cytoplasmic Skp2 expression is increased in human melanoma and correlated with patient survival.

Journal: PloS one 20110101

Title: Bioactivity of miltefosine against aquatic stages of Schistosoma mansoni, Schistosoma haematobium and their snail hosts, supported by scanning electron microscopy.

Journal: Parasites & vectors 20110101

Title: Effect of oral care gel on the quality of life for oral lichen planus in patients with chronic HCV infection.

Journal: Virology journal 20110101

Title: Inhibitory effects of hinokitiol on tyrosinase activity and melanin biosynthesis and its antimicrobial activities.

Journal: Journal of enzyme inhibition and medicinal chemistry 20101201

Title: Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.

Journal: Bioorganic & medicinal chemistry 20101115

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Zn(2+) inhibits coronavirus and arterivirus RNA polymerase activity in vitro and zinc ionophores block the replication of these viruses in cell culture.

Journal: PLoS pathogens 20101101

Title: 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)].

Journal: Acta crystallographica. Section E, Structure reports online 20101101

Title: A urea adduct of bis(hinokitiolato)copper(II).

Journal: Acta crystallographica. Section C, Crystal structure communications 20101001

Title: Bis(hinokitiolato)copper(II): modification (III).

Journal: Acta crystallographica. Section C, Crystal structure communications 20100601

Title: Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases.

Journal: Biochemical and biophysical research communications 20100528

Title: Non-classical anticancer agents: synthesis and biological evaluation of zinc(II) heteroleptic complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20100507

Title: In vitro skin permeation of hinokitiol loaded in vesicles composed of behenyltrimethylammonium chloride and stearic acid.

Journal: Drug development and industrial pharmacy 20100501

Title: Time-kill assay results for a linalool-hinokitiol-based eyelid cleanser for lid hygiene.

Journal: Cornea 20100501

Title: Synthesis of tropolone derivatives and evaluation of their in vitro neuroprotective activity.

Journal: European journal of medicinal chemistry 20100301

Title: Zinc-dependent effects of small molecules on the insulin-sensitive transcription factor FOXO1a and gluconeogenic genes.

Journal: Metallomics : integrated biometal science 20100301

Title: Chemical genetics approach to restoring p27Kip1 reveals novel compounds with antiproliferative activity in prostate cancer cells.

Journal: BMC biology 20100101

Title: 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.

Journal: Cancer letters 20091228

Title: Antimicrobial activity of fullerenes and their hydroxylated derivatives.

Journal: Biocontrol science 20090601

Title: Volatile and non-volatile monoterpenes produced by elicitor-stimulated Cupressus lusitanica cultured cells.

Journal: Journal of plant physiology 20090501

Title: High-performance liquid chromatography with dual-wavelength ultraviolet detection for measurement of hinokitiol in personal care products.

Journal: Journal of cosmetic science 20090101

Title: Harnessing gene expression to identify the genetic basis of drug resistance.

Journal: Molecular systems biology 20090101

Title: High production of beta-thujaplicin glycosides by immobilized plant cells of Nicotiana tabacum.

Journal: Acta biologica Hungarica 20080901

Title: In vivo hair growth promotion effects of cosmetic preparations containing hinokitiol-loaded poly(epsilon-caprolacton) nanocapsules.

Journal: Journal of microencapsulation 20080801

Title: Antifungal properties of ethanolic extract and its active compounds from Calocedrus macrolepis var. formosana (Florin) heartwood.

Journal: Bioresource technology 20080701

Title: Hinokitiol, a natural tropolone derivative, inhibits TNF-alpha production in LPS-activated macrophages via suppression of NF-kappaB.

Journal: Planta medica 20080601

Title: Antifungal mechanism of hinokitiol against Candida albicans.

Journal: Biological & pharmaceutical bulletin 20080401

Title: In vitro permeation study of hinokitiol: effects of vehicles and enhancers.

Journal: Drug delivery 20080101

Title: The mechanism of the bactericidal activity of hinokitiol.

Journal: Biocontrol science 20070901

Title: Growth inhibitory effect of shelf life extending agents on Bacillus subtilis IAM 1026.

Journal: Biocontrol science 20070601

Title: 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.

Journal: The journal of physical chemistry. B 20070222

Title: Baicalein induction of hydroxyl radical formation via 12-lipoxygenase in human platelets: an ESR study.

Journal: Journal of agricultural and food chemistry 20070207

Title: Reactive oxygen species, nitric oxide, and their interactions play different roles in Cupressus lusitanica cell death and phytoalexin biosynthesis.

Journal: The New phytologist 20070101

Title: Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines.

Journal: Biochemical and biophysical research communications 20061208

Title: Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.

Journal: Journal of molecular graphics & modelling 20061101

Title: Lack of hinokitiol (beta-thujaplicin) carcinogenicity in F344/DuCrj rats.

Journal: The Journal of toxicological sciences 20061001

Title: Differential regulation of melanosomal proteins after hinokitiol treatment.

Journal: Journal of dermatological science 20060901

Title: The excellence of Aomori Hiba (Hinokiasunaro) in its use as building materials of Buddhist temples and Shinto shrines.

Journal: Biocontrol science 20060601

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Preferential inhibition of the magnesium-dependent strand transfer reaction of HIV-1 integrase by alpha-hydroxytropolones.

Journal: Molecular pharmacology 20060401

Title: Therapeutic effects of beta-thujaplicin eardrops on canine Malassezia-related otitis externa.

Journal: The Journal of veterinary medical science 20060401

Title: Searching for a new anti-HCV therapy: synthesis and properties of tropolone derivatives.

Journal: Biochemical and biophysical research communications 20060310

Title: Signal transduction and metabolic flux of beta-thujaplicin and monoterpene biosynthesis in elicited Cupressus lusitanica cell cultures.

Journal: Metabolic engineering 20060101

Title: Human metallothionein gene expression is upregulated by beta-thujaplicin: possible involvement of protein kinase C and reactive oxygen species.

Journal: Biological & pharmaceutical bulletin 20060101

Title: Arachidonate 12-lipoxygenases with reference to their selective inhibitors.

Journal: Biochemical and biophysical research communications 20051209

Title: Inhibitory effects of 4-n-butylresorcinol on tyrosinase activity and melanin synthesis.

Journal: Biological & pharmaceutical bulletin 20051201

Title: Prooxidant action of hinokitiol: hinokitiol-iron dependent generation of reactive oxygen species.

Journal: Basic & clinical pharmacology & toxicology 20051201

Title: Effects of beta-thujaplicin on anti-Malassezia pachydermatis remedy for canine otitis externa.

Journal: The Journal of veterinary medical science 20051201

Title: Mosquito larvicidal activity of active constituent derived from Chamaecyparis obtusa leaves against 3 mosquito species.

Journal: Journal of the American Mosquito Control Association 20051201

Title: Oxidative stress in plant cell culture: a role in production of beta-thujaplicin by Cupresssus lusitanica suspension culture.

Journal: Biotechnology and bioengineering 20050605

Title: Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.

Journal: Journal of agricultural and food chemistry 20050323

Title: Fungal diversity from western redcedar fences and their resistance to beta-thujaplicin.

Journal: Antonie van Leeuwenhoek 20050201

Title: Selective inhibition of HIV-1 reverse transcriptase-associated ribonuclease H activity by hydroxylated tropolones.

Journal: Nucleic acids research 20050101

Title: Interaction of silver nanoparticles with HIV-1.

Journal: Journal of nanobiotechnology 20050101

Title: Biological activity of beta-dolabrin, gamma-thujaplicin, and 4-acetyltropolone, hinokitiol-related compounds.

Journal: Biological & pharmaceutical bulletin 20041001

Title: Biological activity of alpha-thujaplicin, the isomer of hinokitiol.

Journal: Biological & pharmaceutical bulletin 20040601

Title: Rapid accumulation and metabolism of polyphosphoinositol and its possible role in phytoalexin biosynthesis in yeast elicitor-treated Cupressus lusitanica cell cultures.

Journal: Planta 20040501

Title: 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: Journal of experimental botany 20040501

Title: Beta-thujaplicin: new quantitative CZE method and adsorption to goethite.

Journal: Journal of agricultural and food chemistry 20040324

Title: Evaluation of developmental toxicity of beta-thujaplicin (hinokitiol) following oral administration during organogenesis in rats.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040301

Title: (-)-Epigallocatechin-3-gallate and hinokitiol reduce melanin synthesis via decreased MITF production.

Journal: Archives of pharmacal research 20040301

Title: 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: Journal of inorganic biochemistry 20040101

Title: Transmission electron microscopy of Schistosoma mansoni cercariae treated with hinokitiol (beta-thujaplicin), a compound for potential skin application against cercarial penetration.

Journal: The Tohoku journal of experimental medicine 20040101

Title: Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines.

Journal: Anticancer research 20040101

Title: [Antimicrobial activity of hinokitiol against Legionella pneumophila].

Journal: Journal of UOEH 20031201

Title: Biological activity of tropolone.

Journal: Biological & pharmaceutical bulletin 20031001

Title: Generation of reactive oxygen species from Hinokitiol under near-UV irradiation.

Journal: Bioscience, biotechnology, and biochemistry 20030901

Title: Multiple signalling pathways mediate fungal elicitor-induced beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures.

Journal: Journal of experimental botany 20030201

Title: 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.

Journal: The Journal of antimicrobial chemotherapy 20030101

Title: Biological activity of 4-acetyltropolone, the minor component of Thujopsis dolabrata SIeb. et Zucc. hondai Mak.

Journal: Biological & pharmaceutical bulletin 20020801

Title: Feedback regulation of beta-thujaplicin production and formation of its methyl ether in a suspension culture of Cupressus lusitanica.

Journal: Phytochemistry 20020701

Title: New lanostanoids, elfvingic acids A-H, from the fruit body of Elfvingia applanata.

Journal: Journal of natural products 20020401

Title: Fungicidal activity of beta-thujaplicin analogues.

Journal: Pest management science 20010901

Title: 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).

Journal: Inorganic chemistry 20010813

Title: Cytotoxic effects of beta-thujaplicin on rat thymocytes and prevention by the compound in tributyltin-induced thymocyte damage.

Journal: Bulletin of environmental contamination and toxicology 20010701

Title: Biological activity of alpha-thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO.

Journal: Biological & pharmaceutical bulletin 20010601

Title: Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.

Journal: Bioscience, biotechnology, and biochemistry 20010501

Title: Improved beta-thujaplicin production in Cupressus lusitanica suspension cultures by fungal elicitor and methyl jasmonate.

Journal: Applied microbiology and biotechnology 20010401

Title: Cytotoxicity of the hinokitiol-related compounds, gamma-thujaplicin and beta-dolabrin.

Journal: Biological & pharmaceutical bulletin 20010301

Title: Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3.

Journal: Cell proliferation 19990201

Title: Thujaplicin-copper chelates inhibit replication of human influenza viruses.

Journal: Antiviral research 19980801

Title: Ouyang WC, et al. Hinokitiol suppresses cancer stemness and oncogenicity in glioma stem cells by Nrf2 regulation. Cancer Chemother Pharmacol. 2017 Aug;80(2):411-419.

Title: Seo JS, et al. Hinokitiol induces DNA demethylation via DNMT1 and UHRF1 inhibition in colon cancer cells. BMC Cell Biol. 2017 Feb 27;18(1):14.

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