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beta-thujaplicin

Chemical Structure

General Material Information

Preferred name beta-thujaplicin
Trivial Name Hinokitiol
Short Description 2,4,6-cycloheptatrien-1-one, 2-hydroxy-6-(1-methylethyl)-
Formula C10 H12 O2
CAS Number 499-44-5
ECHA Number 207-880-7
FDA UNII U5335D6EBI
Nikkaji Number J6.176J
Beilstein Number 2045206
MDL MFCD00059582
xLogP3-AA 2.10 (est)
Bio Activity Summary External link
NMR Predictor External link
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-
  • 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
  • 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-
  • 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-isopropyl-
  • 2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one
  • 2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one
  • 4-Isopropyltropolone
  • β-Thujaplicin
  • β-Thujaplicine
  • β-Isopropyltropolon
  • IPT
  • 6-Isopropyltropolone
  • Hyka 1
  • S-HT
  • HT-SF
  • NSC 18804
  • Kisei Pro-Sol N
  • Hinokitiol S-HT
  • beta-Thujaplicine
  • H 0142
  • 2-Hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
  • 2-Hydroxy-4-(propan-2-yl)cyclohepta-2,4,6-trien-1-one

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Literature & References

2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:499-44-5
Pubchem (cid):3611
Pubchem (sid):134977780
Publications by PubMed
Toxicity of hiba oil constituents and spray formulations to American house dust mites and copra mites.
A novel synthetic pathway for tropolone ring formation via the olefin monoterpene intermediate terpinolene in cultured Cupressus lusitanica cells.
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.
Hinokitiol, a natural tropolone derivative, offers neuroprotection from thromboembolic stroke in vivo.
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.
Effect of mouth cleaning with hinokitiol-containing gel on oral malodor: a randomized, open-label pilot study.
Tetsuo Nozoe's "Autograph Books by Chemists 1953-1994": an essay.
Hinokitiol inhibits platelet activation ex vivo and thrombus formation in vivo.
In vitro antimicrobial and anticancer potential of hinokitiol against oral pathogens and oral cancer cell lines.
Stress-related activities induced by predator odor may become indistinguishable by hinokitiol odor.
In vitro and in vivo anti-plasmodial activity of essential oils, including hinokitiol.
The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs.
In vitro and in vivo therapeutics of β-thujaplicin on LPS-induced inflammation in macrophages and septic shock in mice.
Preventive effects of β-thujaplicin against UVB-induced MMP-1 and MMP-3 mRNA expressions in skin fibroblasts.
Effects of a combination of hinokitiol (β-thujaplicin) and an organic acid mixture on ruminal fermentation in heifers fed a high-grain diet.
In vitro Na+/K+-ATPase inhibitory activity and antimicrobial activity of sesquiterpenes isolated from Thujopsis dolabrata.
A 13-week subchronic toxicity study of hinokitiol administered in the diet to F344 rats.
Zinc-dependent effects of small molecules on the insulin-sensitive transcription factor FOXO1a and gluconeogenic genes.
Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.
Inhibitory effects of hinokitiol on tyrosinase activity and melanin biosynthesis and its antimicrobial activities.
Hinokitiol activates the hypoxia-inducible factor (HIF) pathway through inhibition of HIF hydroxylases.
Time-kill assay results for a linalool-hinokitiol-based eyelid cleanser for lid hygiene.
In vitro skin permeation of hinokitiol loaded in vesicles composed of behenyltrimethylammonium chloride and stearic acid.
Synthesis of tropolone derivatives and evaluation of their in vitro neuroprotective activity.
High-performance liquid chromatography with dual-wavelength ultraviolet detection for measurement of hinokitiol in personal care products.
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.
Effects of leaching on fungal growth and decay of western redcedar.
Volatile and non-volatile monoterpenes produced by elicitor-stimulated Cupressus lusitanica cultured cells.
Antiviral activity of the zinc ionophores pyrithione and hinokitiol against picornavirus infections.
High production of beta-thujaplicin glycosides by immobilized plant cells of Nicotiana tabacum.
Hinokitiol, a natural tropolone derivative, inhibits TNF-alpha production in LPS-activated macrophages via suppression of NF-kappaB.
In vivo hair growth promotion effects of cosmetic preparations containing hinokitiol-loaded poly(epsilon-caprolacton) nanocapsules.
Antifungal mechanism of hinokitiol against Candida albicans.
In vitro permeation study of hinokitiol: effects of vehicles and enhancers.
Antifungal properties of ethanolic extract and its active compounds from Calocedrus macrolepis var. formosana (Florin) heartwood.
The mechanism of the bactericidal activity of hinokitiol.
Growth inhibitory effect of shelf life extending agents on Bacillus subtilis IAM 1026.
Reactive oxygen species, nitric oxide, and their interactions play different roles in Cupressus lusitanica cell death and phytoalexin biosynthesis.
Analysis of western redcedar (Thuja plicata Donn) heartwood components by HPLC as a possible screening tool for trees with enhanced natural durability.
Lack of hinokitiol (beta-thujaplicin) carcinogenicity in F344/DuCrj rats.
Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines.
The excellence of Aomori Hiba (Hinokiasunaro) in its use as building materials of Buddhist temples and Shinto shrines.
Differential regulation of melanosomal proteins after hinokitiol treatment.
Therapeutic effects of beta-thujaplicin eardrops on canine Malassezia-related otitis externa.
Mosquito larvicidal activity of active constituent derived from Chamaecyparis obtusa leaves against 3 mosquito species.
Effects of beta-thujaplicin on anti-Malassezia pachydermatis remedy for canine otitis externa.
Human metallothionein gene expression is upregulated by beta-thujaplicin: possible involvement of protein kinase C and reactive oxygen species.
Prooxidant action of hinokitiol: hinokitiol-iron dependent generation of reactive oxygen species.
Inhibitory effects of 4-n-butylresorcinol on tyrosinase activity and melanin synthesis.
Signal transduction and metabolic flux of beta-thujaplicin and monoterpene biosynthesis in elicited Cupressus lusitanica cell cultures.
In vitro inhibitory effects of hinokitiol on proliferation of Chlamydia trachomatis.
Oxidative stress in plant cell culture: a role in production of beta-thujaplicin by Cupresssus lusitanica suspension culture.
Fungal diversity from western redcedar fences and their resistance to beta-thujaplicin.
Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.
Protection by tropolones against H2O2-induced DNA damage and apoptosis in cultured Jurkat cells.
Selective inhibition of HIV-1 reverse transcriptase-associated ribonuclease H activity by hydroxylated tropolones.
Biological activity of beta-dolabrin, gamma-thujaplicin, and 4-acetyltropolone, hinokitiol-related compounds.
Biological activity of alpha-thujaplicin, the isomer of hinokitiol.
Cytotoxic activity of deferiprone, maltol and related hydroxyketones against human tumor cell lines.
(-)-Epigallocatechin-3-gallate and hinokitiol reduce melanin synthesis via decreased MITF production.
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.
Beta-thujaplicin: new quantitative CZE method and adsorption to goethite.
Evaluation of developmental toxicity of beta-thujaplicin (hinokitiol) following oral administration during organogenesis in rats.
Rapid accumulation and metabolism of polyphosphoinositol and its possible role in phytoalexin biosynthesis in yeast elicitor-treated Cupressus lusitanica cell cultures.
Transmission electron microscopy of Schistosoma mansoni cercariae treated with hinokitiol (beta-thujaplicin), a compound for potential skin application against cercarial penetration.
[Antimicrobial activity of hinokitiol against Legionella pneumophila].
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.
Monoterpenes produced by Cupressus lusitanica cultured cells including a novel monoterpene (1R, 2S, 6S)-(+)-1,6-epoxy-4(8)-p-menthen-2-ol [corrected].
Generation of reactive oxygen species from Hinokitiol under near-UV irradiation.
Multiple signalling pathways mediate fungal elicitor-induced beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures.
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.
Biological activity of 4-acetyltropolone, the minor component of Thujopsis dolabrata SIeb. et Zucc. hondai Mak.
Feedback regulation of beta-thujaplicin production and formation of its methyl ether in a suspension culture of Cupressus lusitanica.
Fungicidal activity of beta-thujaplicin analogues.
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.
Biological activity of alpha-thujaplicin, the minor component of Thujopsis dolabrata SIEB. et ZUCC. var. hondai MAKINO.
Cytotoxic effects of beta-thujaplicin on rat thymocytes and prevention by the compound in tributyltin-induced thymocyte damage.
Improved beta-thujaplicin production in Cupressus lusitanica suspension cultures by fungal elicitor and methyl jasmonate.
Cytotoxicity of the hinokitiol-related compounds, gamma-thujaplicin and beta-dolabrin.
Identification of a compound in Chamaecyparis taiwanensis inhibiting the ice-nucleating activity of Pseudomonas fluorescens KUIN-1.
Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase.
Antifungal activity of Hinokitiol-related compounds on wood-rotting fungi and their insecticidal activities.
Phytogrowth-Inhibitory activities of beta-dolabrin and gamma-thujaplicin, hinokitiol-related compounds and constituents of Thujopsis dolabrata Sieb. et Zucc. var hondai Makino.
Apoptosis during iron chelator-induced differentiation in F9 embryonal carcinoma cells.
Teratogenicity of thujaplicin in ICR mice.
Antimicrobial activity and metalloprotease inhibition of hinokitiol-related compounds, the constituents of Thujopsis dolabrata S. and Z. hondai MAK.
Multi-enzymatic glucosylation using Eucalyptus UDP-glucosyltransferase coupled UDPglucose-fermentation by bakers' yeast.
Induction of apoptosis by hinokitiol, a potent iron chelator, in teratocarcinoma F9 cells is mediated through the activation of caspase-3.
Beta-thujaplicin zinc chelate induces apoptosis in mouse high metastatic melanoma B16BL6 cells.
Mechanism of mitochondrial dysfunction and cytotoxicity induced by tropolones in isolated rat hepatocytes.
Thujaplicin-copper chelates inhibit replication of human influenza viruses.
Effects of zinc oxide on the attachment of Staphylococcus aureus strains.
Inhibitory effect of beta-thujaplicin on ultraviolet B-induced apoptosis in mouse keratinocytes.
Biological activity of purpurogallin.
Induction of differentiation of embryonal carcinoma F9 cells by iron chelators.
Hinokitiol induces differentiation of teratocarcinoma F9 cells.
[On the antibacterial effect of hinokitiol against Staphylococcus aureus showing double zone phenomenon].
Cytotoxic effect of hinokitiol and tropolone on the growth of mammalian cells and on blastogenesis of mouse splenic T cells.
[Study on the development of biological-active compounds after the model of natural products].
High-performance liquid chromatographic determination of hinokitiol in cosmetics by the formation of difluoroborane compounds.
[A clinical re-evaluation of an Hinoporon on periodontal disease using the double blind method].
[Methylation of hinokitiol and 7-iodohinokitiol and the syntheses of Schiff bases of hydrazinotropone derivatives and 5-aminohinokitiol].
Calcium-independent release of [3H]dopamine by veratridine in pargyline- and reserpine-treated corpus striatum.
Allergic contact dermatitis to pyridoxine ester and hinokitiol.
The multifunctional actions of beta-thujaplicin on the oxidative energy transformations as a consequence of its lipophilic and chelating properties.
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.
The extraneuronal accumulation of isoprenaline in trachea and atria of guinea-pig and cat: a fluorescence histochemical study.
The uptake kinetics and metabolism of extraneuronal noradrenaline in guinea-pig trachea as studied with quantitative fluorescence microphotometry.
Antibacterial activity of beta-thujaplicin.
The effect of light on the antibacterial activity of beta-thujaplicin.
Synethesis of beta-dolabrin from beta-thujaplicin (hinokitiol).
Antibiotic substances from the heart wood of Thuja plicata D. Don; the constitution of beta-thujaplicin.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09904
HMDB (The Human Metabolome Database):HMDB35213
FooDB:FDB013860
Export Tariff Code:2914.40.9000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 164.20404052734
Melting Point 48 to 53°C @ 760 mm Hg
Boiling Point 303 to 304°C @ 760 mm Hg
Vapor Pressure 8.9E-5 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 1.137 est
Solubility
alcohol Yes
water, 1592 mg/L @ 25 °C (est) Yes
water, 1200 mg/L @ 25 °C (exp) Yes
water No
Stability
detergent Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Woody
phenolic, woody, mossy
Odor strength medium
Substantivity 48 hour(s) at 100.00 %
General comment At 100.00 %. phenolic woody mossy
Can give woody-mossy character in fragrances. Has antibacterial and preservative properties that are useful in drug and cosmetic applications. Phenol-like and woody

Occurrences

Potential Uses

Applications
Odor purposes Balsam, Cedar, Herbal, Moss, Oriental, Woody
Other purposes Antibacterial agents, Preservatives
Cosmetic purposes Antistatic agents, Hair conditioning

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 500 mg/kg
BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES
National Technical Information Service. Vol. OTS0570591

intravenous-mouse LD50 128 mg/kg
BEHAVIORAL: ANALGESIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakugaku Zasshi. Journal of Pharmacy. Vol. 91, Pg. 550, 1971.

intraperitoneal-mouse LD50 85 mg/kg
Journal of Medicinal Chemistry. Vol. 6, Pg. 755, 1963.

Dermal Toxicity:
skin-rabbit LD50 > 2000 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: FOOD INTAKE (ANIMAL)
National Technical Information Service. Vol. OTS0570591

subcutaneous-mouse LD50 541 mg/kg
BEHAVIORAL: ANALGESIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakugaku Zasshi. Journal of Pharmacy. Vol. 91, Pg. 550, 1971.

subcutaneous-guinea pig LD50 500 mg/kg
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 48, Pg. 722, 1959.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
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.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):499-44-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3611
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
Chemidplus:0000499445
RTECS:GU4200000 for cas# 499-44-5