Hinokitiol

Modify Date: 2024-01-02 18:01:01

Hinokitiol Structure
Hinokitiol structure
 Common Name Hinokitiol
CAS Number 499-44-5 Molecular Weight 164.201
Density 1.1±0.1 g/cm3 Boiling Point 303.4±35.0 °C at 760 mmHg
Molecular Formula C10H12O2 Melting Point 50-52 °C(lit.)
MSDS Chinese USA Flash Point 128.1±18.5 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Hinokitiol


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.

 Names

Name β-thujaplicin
Synonym More Synonyms

 Hinokitiol 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
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.

 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

 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
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

 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%

 Articles32

More 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...

 Synonyms

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
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