beta-thujaplicin
2,4,6-cycloheptatrien-1-one, 2-hydroxy-6-(1-methylethyl)-
Identification
| Name | beta-thujaplicin |
| IUPAC | 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one |
| CAS Number | 499-44-5 |
| EINECS | 207-880-7 |
| FDA UNII | U5335D6EBI |
| Molecular Formula | C10 H12 O2 |
| Molecular Weight | 164.20404000 |
| MDL Number | MFCD00059582 |
| Nikkaji Number | J6.176J |
| Beilstein | 2045206 |
Regulatory
Physical Properties
| Appearance | colorless to pale yellow crystals (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 48.00 to 53.00 °C. @ 760.00 mm Hg |
| Boiling Point | 140.00 °C. @ 10.00 mm Hg, 303.00 to 304.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.000089 mmHg @ 25.00 °C. (est) |
| Flash Point | > 212.00 °F. TCC ( > 100.00 °C. ) |
| logP (o/w) | 1.137 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
| Stability | detergent |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antistatic agents |
Organoleptic Properties
| Odor Strength | medium |
| Substantivity | 48 hour(s) at 100.00 % |
| Odor Description |
at 100.00 %. Phenol-like and woody
|
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 500 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 2000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for beta-thujaplicin usage levels up to | 0.1000 % in the fragrance concentrate. |
| Recommendation for beta-thujaplicin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2,4,6-
cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-
2,4,6-
cycloheptatrien-1-one, 2-hydroxy-4-isopropyl-
2,4,6-
cycloheptatrien-1-one, 2-hydroxy-6-(1-methylethyl)-
hinokitiol
hinokitiol crystals
hinokitiol crystals (takasago)
hinokitol
2-
hydroxy-4-(1-methyl ethyl)-2,4,6-cycloheptatrien-1-one
2-
hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one
2-
hydroxy-4-(methylethyl)cyclohepta-2,4,6-trien-1-one
2-
hydroxy-4-isopropyl-2,4, 6-cycloheptatrien-1-one
2-
hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-one
2-
hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one
2-
hydroxy-4-isopropyl-cyclohepta-2,4,6-trienone
2-
hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-one
2-
hydroxy-4-isopropylcyclohepta-2,4,6-trienone
2-
hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
2-
hydroxy-6-isopropyl-2,4,6-cycloheptatrien-1-one
2-
hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
beta-iso
propyl tropolon
4-iso
propyl tropolone
iso
propyl tropolone
4-iso
propyltropolone
beta-
thujaplicin
beta-
thujaplicine
tropolone, 4-isopropyl-
PubMed:
Toxicity of hiba oil constituents and spray formulations to American house dust mites and copra mites.
PubMed:
A novel synthetic pathway for tropolone ring formation via the olefin monoterpene intermediate terpinolene in cultured Cupressus lusitanica cells.
PubMed:
Hinokitiol inhibits cell growth through induction of S-phase arrest and apoptosis in human colon cancer cells and suppresses tumor growth in a mouse xenograft experiment.
PubMed:
Hinokitiol, a natural tropolone derivative, offers neuroprotection from thromboembolic stroke in vivo.
PubMed:
Determination of hinokitiol in skin lotion by high-performance liquid chromatography-ultraviolet detection after precolumn derivatization with 4-fluoro-7-nitro-2,1,3-benzoxadiazole.
PubMed:
Effect of mouth cleaning with hinokitiol-containing gel on oral malodor: a randomized, open-label pilot study.
PubMed:
Tetsuo Nozoe's "Autograph Books by Chemists 1953-1994": an essay.
PubMed:
Hinokitiol inhibits platelet activation ex vivo and thrombus formation in vivo.
PubMed:
In vitro antimicrobial and anticancer potential of hinokitiol against oral pathogens and oral cancer cell lines.
PubMed:
Stress-related activities induced by predator odor may become indistinguishable by hinokitiol odor.
PubMed:
In vitro and in vivo anti-plasmodial activity of essential oils, including hinokitiol.
PubMed:
The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs.
PubMed:
In vitro and in vivo therapeutics of β-thujaplicin on LPS-induced inflammation in macrophages and septic shock in mice.
PubMed:
Preventive effects of β-thujaplicin against UVB-induced MMP-1 and MMP-3 mRNA expressions in skin fibroblasts.
PubMed:
Effects of a combination of hinokitiol (β-thujaplicin) and an organic acid mixture on ruminal fermentation in heifers fed a high-grain diet.
PubMed:
In vitro Na+/K+-ATPase inhibitory activity and antimicrobial activity of sesquiterpenes isolated from Thujopsis dolabrata.
PubMed:
A 13-week subchronic toxicity study of hinokitiol administered in the diet to F344 rats.
PubMed:
Zinc-dependent effects of small molecules on the insulin-sensitive transcription factor FOXO1a and gluconeogenic genes.
PubMed:
Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.
PubMed:
Inhibitory effects of hinokitiol on tyrosinase activity and melanin biosynthesis and its antimicrobial activities.
PubMed:
Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases.
PubMed:
Time-kill assay results for a linalool-hinokitiol-based eyelid cleanser for lid hygiene.
PubMed:
In vitro skin permeation of hinokitiol loaded in vesicles composed of behenyltrimethylammonium chloride and stearic acid.
PubMed:
Synthesis of tropolone derivatives and evaluation of their in vitro neuroprotective activity.
PubMed:
High-performance liquid chromatography with dual-wavelength ultraviolet detection for measurement of hinokitiol in personal care products.
PubMed:
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.
PubMed:
Effects of leaching on fungal growth and decay of western redcedar.
PubMed:
Volatile and non-volatile monoterpenes produced by elicitor-stimulated Cupressus lusitanica cultured cells.
PubMed:
Antiviral activity of the zinc ionophores pyrithione and hinokitiol against picornavirus infections.
PubMed:
High production of beta-thujaplicin glycosides by immobilized plant cells of Nicotiana tabacum.
PubMed:
Hinokitiol, a natural tropolone derivative, inhibits TNF-alpha production in LPS-activated macrophages via suppression of NF-kappaB.
PubMed:
In vivo hair growth promotion effects of cosmetic preparations containing hinokitiol-loaded poly(epsilon-caprolacton) nanocapsules.
PubMed:
Antifungal mechanism of hinokitiol against Candida albicans.
PubMed:
In vitro permeation study of hinokitiol: effects of vehicles and enhancers.
PubMed:
Antifungal properties of ethanolic extract and its active compounds from Calocedrus macrolepis var. formosana (Florin) heartwood.
PubMed:
The mechanism of the bactericidal activity of hinokitiol.
PubMed:
Growth inhibitory effect of shelf life extending agents on Bacillus subtilis IAM 1026.
PubMed:
Reactive oxygen species, nitric oxide, and their interactions play different roles in Cupressus lusitanica cell death and phytoalexin biosynthesis.
PubMed:
Analysis of western redcedar (Thuja plicata Donn) heartwood components by HPLC as a possible screening tool for trees with enhanced natural durability.
PubMed:
Lack of hinokitiol (beta-thujaplicin) carcinogenicity in F344/DuCrj rats.
PubMed:
Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines.
PubMed:
The excellence of Aomori Hiba (Hinokiasunaro) in its use as building materials of Buddhist temples and Shinto shrines.
PubMed:
Differential regulation of melanosomal proteins after hinokitiol treatment.
PubMed:
Therapeutic effects of beta-thujaplicin eardrops on canine Malassezia-related otitis externa.
PubMed:
Mosquito larvicidal activity of active constituent derived from Chamaecyparis obtusa leaves against 3 mosquito species.
PubMed:
Effects of beta-thujaplicin on anti-Malassezia pachydermatis remedy for canine otitis externa.
PubMed:
Human metallothionein gene expression is upregulated by beta-thujaplicin: possible involvement of protein kinase C and reactive oxygen species.
PubMed:
Prooxidant action of hinokitiol: hinokitiol-iron dependent generation of reactive oxygen species.
PubMed:
Inhibitory effects of 4-n-butylresorcinol on tyrosinase activity and melanin synthesis.
PubMed:
Signal transduction and metabolic flux of beta-thujaplicin and monoterpene biosynthesis in elicited Cupressus lusitanica cell cultures.
PubMed:
In vitro inhibitory effects of hinokitiol on proliferation of Chlamydia trachomatis.
PubMed:
Oxidative stress in plant cell culture: a role in production of beta-thujaplicin by Cupresssus lusitanica suspension culture.
PubMed:
Fungal diversity from western redcedar fences and their resistance to beta-thujaplicin.
PubMed:
Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.
PubMed:
Protection by tropolones against H2O2-induced DNA damage and apoptosis in cultured Jurkat cells.
PubMed:
Selective inhibition of HIV-1 reverse transcriptase-associated ribonuclease H activity by hydroxylated tropolones.
PubMed:
Biological activity of beta-dolabrin, gamma-thujaplicin, and 4-acetyltropolone, hinokitiol-related compounds.
PubMed:
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
PubMed:
Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines.
PubMed:
(-)-Epigallocatechin-3-gallate and hinokitiol reduce melanin synthesis via decreased MITF production.
PubMed:
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.
PubMed:
Beta-thujaplicin: new quantitative CZE method and adsorption to goethite.
PubMed:
Evaluation of developmental toxicity of beta-thujaplicin (hinokitiol) following oral administration during organogenesis in rats.
PubMed:
Rapid accumulation and metabolism of polyphosphoinositol and its possible role in phytoalexin biosynthesis in yeast elicitor-treated Cupressus lusitanica cell cultures.
PubMed:
Transmission electron microscopy of Schistosoma mansoni cercariae treated with hinokitiol (beta-thujaplicin), a compound for potential skin application against cercarial penetration.
PubMed:
[Antimicrobial activity of hinokitiol against Legionella pneumophila].
PubMed:
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.
PubMed:
Monoterpenes produced by Cupressus lusitanica cultured cells including a novel monoterpene (1R, 2S, 6S)-(+)-1,6-epoxy-4(8)-p-menthen-2-ol [corrected].
PubMed:
Generation of reactive oxygen species from Hinokitiol under near-UV irradiation.
PubMed:
Multiple signalling pathways mediate fungal elicitor-induced beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures.
PubMed:
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.
PubMed:
Biological activity of 4-acetyltropolone, the minor component of Thujopsis dolabrata SIeb. et Zucc. hondai Mak.
PubMed:
Feedback regulation of beta-thujaplicin production and formation of its methyl ether in a suspension culture of Cupressus lusitanica.
PubMed:
Fungicidal activity of beta-thujaplicin analogues.
PubMed:
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.
PubMed:
Biological activity of alpha-thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO.
PubMed:
Cytotoxic effects of beta-thujaplicin on rat thymocytes and prevention by the compound in tributyltin-induced thymocyte damage.
PubMed:
Improved beta-thujaplicin production in Cupressus lusitanica suspension cultures by fungal elicitor and methyl jasmonate.
PubMed:
Cytotoxicity of the hinokitiol-related compounds, gamma-thujaplicin and beta-dolabrin.
PubMed:
Identification of a compound in Chamaecyparis taiwanensis inhibiting the ice-nucleating activity of Pseudomonas fluorescens KUIN-1.
PubMed:
Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase.
PubMed:
Antifungal activity of Hinokitiol-related compounds on wood-rotting fungi and their insecticidal activities.
PubMed:
Phytogrowth-Inhibitory activities of beta-dolabrin and gamma-thujaplicin, hinokitiol-related compounds and constituents of Thujopsis dolabrata Sieb. et Zucc. var hondai Makino.
PubMed:
Apoptosis during iron chelator-induced differentiation in F9 embryonal carcinoma cells.
PubMed:
Teratogenicity of thujaplicin in ICR mice.
PubMed:
Antimicrobial activity and metalloprotease inhibition of hinokitiol-related compounds, the constituents of Thujopsis dolabrata S. and Z. hondai MAK.
PubMed:
Multi-enzymatic glucosylation using Eucalyptus UDP-glucosyltransferase coupled UDPglucose-fermentation by bakers' yeast.
PubMed:
Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3.
PubMed:
Beta-thujaplicin zinc chelate induces apoptosis in mouse high metastatic melanoma B16BL6 cells.
PubMed:
Mechanism of mitochondrial dysfunction and cytotoxicity induced by tropolones in isolated rat hepatocytes.
PubMed:
Thujaplicin-copper chelates inhibit replication of human influenza viruses.
PubMed:
Effects of zinc oxide on the attachment of Staphylococcus aureus strains.
PubMed:
Inhibitory effect of beta-thujaplicin on ultraviolet B-induced apoptosis in mouse keratinocytes.
PubMed:
Biological activity of purpurogallin.
PubMed:
Induction of differentiation of embryonal carcinoma F9 cells by iron chelators.
PubMed:
Hinokitiol induces differentiation of teratocarcinoma F9 cells.
PubMed:
[On the antibacterial effect of hinokitiol against Staphylococcus aureus showing double zone phenomenon].
PubMed:
Cytotoxic effect of hinokitiol and tropolone on the growth of mammalian cells and on blastogenesis of mouse splenic T cells.
PubMed:
[Study on the development of biological-active compounds after the model of natural products].
PubMed:
High-performance liquid chromatographic determination of hinokitiol in cosmetics by the formation of difluoroborane compounds.
PubMed:
[A clinical re-evaluation of an Hinoporon on periodontal disease using the double blind method].
PubMed:
[Methylation of hinokitiol and 7-iodohinokitiol and the syntheses of Schiff bases of hydrazinotropone derivatives and 5-aminohinokitiol].
PubMed:
Calcium-independent release of [3H]dopamine by veratridine in pargyline- and reserpine-treated corpus striatum.
PubMed:
Allergic contact dermatitis to pyridoxine ester and hinokitiol.
PubMed:
The multifunctional actions of beta-thujaplicin on the oxidative energy transformations as a consequence of its lipophilic and chelating properties.
PubMed:
Comparison of the effects of tropolone, beta-thujaplicin and U-0521 on the extraneuronal accumulation of isoprenaline in guinea-pig trachealis smooth muscle cells. A quantitative fluorescence histochemical study.
PubMed:
The extraneuronal accumulation of isoprenaline in trachea and atria of guinea-pig and cat: a fluorescence histochemical study.
PubMed:
The uptake kinetics and metabolism of extraneuronal noradrenaline in guinea-pig trachea as studied with quantitative fluorescence microphotometry.
PubMed:
Antibacterial activity of beta-thujaplicin.
PubMed:
The effect of light on the antibacterial activity of beta-thujaplicin.
PubMed:
Synethesis of beta-dolabrin from beta-thujaplicin (hinokitiol).
PubMed:
Antibiotic substances from the heart wood of Thuja plicata D. Don; the constitution of beta-thujaplicin.