Hinokitiol

Names

[ CAS No. ]:
499-44-5

[ Name ]:
Hinokitiol

[Synonym ]:
Isopropyltropolone
2-Hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
B-THUJAPLICIN
2,4,6-cycloheptatrien-1-one, 2-hydroxy-6-(1-methylethyl)-
2-Hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-on
beta-thujaplicin
4-ISOPROPYLTROPOLONE
MFCD00040180
2-Hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-one
2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-
β-Thujaplicine
EINECS 207-880-7
Hinokitiol
β-Thujaplicin
Hinokitol
2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one
2-hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one

Biological Activity

[Description]:

Hinokitiol is a component of essential oils isolated from Chymacyparis obtusa, reduces Nrf2 expression, and decreases DNMT1 and UHRF1 mRNA and protein expression, with anti-infective, anti-oxidative, and anti-tumor activities.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> DNA Methyltransferase

Signaling Pathways >> NF-κB >> Keap1-Nrf2

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

Research Areas >> Infection

[Target]

DNMT1

Nrf2

[In Vitro]

In U87MG and T98G glioma cell lines, hinokitiol demonstrates a dose-dependent decrease in viability, with IC50 values of 316.5 ± 35.5 and 152.5 ± 25.3 µM, respectively. Hinokitiol represses ALDH activity and self-renewal ability in glioma stem cells, and inhibits in vitro oncogenicity. Hinokitiol also reduces Nrf2 expression in glioma stem cells in a dose-dependent manner[1]. Hinokitiol (0-100 μM) inhibits colon cancer cell growth in a dose- and time-dependent manner. Hinokitiol (5, 10 μM) decreases DNMT1 and UHRF1 mRNA and protein expression, and increases TET1 expression via enhancement of 5hmC level in HCT-116 cells. Furthermore, hinokitiol reduces methylation status and restores mRNA expression of MGMT, CHST10, and BTG4 genes[2].

[Cell Assay]

U87MG and T98G glioma cells are cultured in Dulbecco's modified Eagle's medium with Ham's F12 medium (DMEM/F-12) containing 10% fetal bovine serum. Cell viability is determined using MTT to evaluate the cytotoxicity of hinokitiol. Cells are seeded in 24-well plates (1×105 cells/well) in the presence of various concentration of hinokitiol or vehicle at 37°C for 24 h followed by incubation with MTT reagent. The blue formazan crystals of viable cells are dissolved in DMSO and then evaluated spectrophotometrically at 570 nm. DMSO-treated group is set as 100%, and data are presented as percentage of DMSO control. IC50 values are calculated by the GraFit software.

[References]

[1]. 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.

[2]. 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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
303.4±35.0 °C at 760 mmHg

[ Melting Point ]:
50-52 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂O₂

[ Molecular Weight ]:
164.201

[ Flash Point ]:
128.1±18.5 °C

[ Exact Mass ]:
164.083725

[ PSA ]:
37.30000

[ LogP ]:
1.89

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.554

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GU4200000

CHEMICAL NAME :: 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-isopropyl-

CAS REGISTRY NUMBER :: 499-44-5

BEILSTEIN REFERENCE NO. :: 2045206

LAST UPDATED :: 199710

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C10-H12-O2

MOLECULAR WEIGHT :: 164.22

WISWESSER LINE NOTATION :: L7VJ BQ DY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal) Gastrointestinal - other changes

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570591

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 85 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 6,755,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 541 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - analgesia Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 91,550,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 128 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - analgesia Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 91,550,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - food intake (animal)

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570591

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAPMA8 Journal of the American Pharmaceutical Association, Scientific Edition. (Washington, DC) V.29-49, 1940-60. For publisher information, see JPMSAE. Volume(issue)/page/year: 48,722,1959

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
GU4200000

[ HS Code ]:
2914400090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914400090

[ Summary ]:
2914400090 other ketone-alcohols and ketone-aldehydes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

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.

J. Cosmet. Sci. 64(5) , 381-9, (2013)

Hinokitiol, a potent, broad-spectrum antibacterial agent, is a component of various personal care products. In this study, the concentration of hinokitiol in skin lotion was analyzed by means of high-...

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

Org. Biomol. Chem. 10(43) , 8597-604, (2012)

A direct route to analogs of the naturally occurring tropolone β-thujaplicin has been developed in just four steps from furan. Using this method, a series of derivatives were synthesized and evaluated...

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

J. Cosmet. Sci. 60(5) , 519-25, (2009)

Hinokitiol is found in the heartwood of several cupressaceous plants and is frequently added to cosmetic products such as hair restorers, skin lotions, and body soaps because of its potent and broad-s...

Related Compounds

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