Hinokitiol
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 112137

CAS#: 499-44-5

Description: Hinokitiol inhibits proliferation of HCT-116 and SW-620 colon cancer cells (IC50s = 4.5 and 4.4 µM, respectively), arrests the cell cycle, and induces apoptosis.

Chemical Structure

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Hinokitiol
CAS# 499-44-5
Instruction

Theoretical Analysis

MedKoo Cat#: 112137
Name: Hinokitiol
CAS#: 499-44-5
Chemical Formula: C10H12O2
Exact Mass: 164.08
Molecular Weight: 164.200
Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size Price Availability Quantity
1g USD 250 2 Weeks
5g USD 550 2 Weeks
10g USD 750 2 Weeks
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Synonym: Hinokitiol; NSC 18804; β-Thujaplicin; 4-isopropyl Tropolone; NSC18804; βThujaplicin; 4isopropyl Tropolone; NSC-18804; β Thujaplicin; 4 isopropyl Tropolone

IUPAC/Chemical Name: 2-hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-one

InChi Key: FUWUEFKEXZQKKA-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)

SMILES Code: O=C1C(O)=CC(C(C)C)=CC=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 182.70
Ethanol 20.0 121.80

Preparing Stock Solutions

The following data is based on the product molecular weight 164.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Wang WK, Lin ST, Chang WW, Liu LW, Li TY, Kuo CY, Hsieh JL, Lee CH. Hinokitiol induces autophagy in murine breast and colorectal cancer cells. Environ Toxicol. 2016 Jan;31(1):77-84. doi: 10.1002/tox.22023. Epub 2014 Jul 12. PMID: 25044443.


2: Jayakumar T, Liu CH, Wu GY, Lee TY, Manubolu M, Hsieh CY, Yang CH, Sheu JR. Hinokitiol Inhibits Migration of A549 Lung Cancer Cells via Suppression of MMPs and Induction of Antioxidant Enzymes and Apoptosis. Int J Mol Sci. 2018 Mar 22;19(4):939. doi: 10.3390/ijms19040939. PMID: 29565268; PMCID: PMC5979393.


3: Chen HY, Cheng WP, Chiang YF, Hong YH, Ali M, Huang TC, Wang KL, Shieh TM, Chang HY, Hsia SM. Hinokitiol Exhibits Antitumor Properties through Induction of ROS-Mediated Apoptosis and p53-Driven Cell-Cycle Arrest in Endometrial Cancer Cell Lines (Ishikawa, HEC-1A, KLE). Int J Mol Sci. 2021 Jul 31;22(15):8268. doi: 10.3390/ijms22158268. PMID: 34361036; PMCID: PMC8348875.


4: Seo JS, Choi YH, Moon JW, Kim HS, Park SH. Hinokitiol induces DNA demethylation via DNMT1 and UHRF1 inhibition in colon cancer cells. BMC Cell Biol. 2017 Feb 27;18(1):14. doi: 10.1186/s12860-017-0130-3. PMID: 28241740; PMCID: PMC5327573.


5: Ouyang WC, Liao YW, Chen PN, Lu KH, Yu CC, Hsieh PL. Hinokitiol suppresses cancer stemness and oncogenicity in glioma stem cells by Nrf2 regulation. Cancer Chemother Pharmacol. 2017 Aug;80(2):411-419. doi: 10.1007/s00280-017-3381-y. Epub 2017 Jul 6. PMID: 28685346.


6: Tu DG, Yu Y, Lee CH, Kuo YL, Lu YC, Tu CW, Chang WW. Hinokitiol inhibits vasculogenic mimicry activity of breast cancer stem/progenitor cells through proteasome-mediated degradation of epidermal growth factor receptor. Oncol Lett. 2016 Apr;11(4):2934-2940. doi: 10.3892/ol.2016.4300. Epub 2016 Mar 2. PMID: 27073579; PMCID: PMC4812586.


7: Chen SM, Wang BY, Lee CH, Lee HT, Li JJ, Hong GC, Hung YC, Chien PJ, Chang CY, Hsu LS, Chang WW. Hinokitiol up-regulates miR-494-3p to suppress BMI1 expression and inhibits self-renewal of breast cancer stem/progenitor cells. Oncotarget. 2017 Jun 27;8(44):76057-76068. doi: 10.18632/oncotarget.18648. PMID: 29100291; PMCID: PMC5652685.


8: Yang HW, Lu MY, Chiu YW, Liao YW, Huang YF, Ju Chueh P, Hsieh PL, Yu CC. Hinokitiol ablates myofibroblast activation in precancerous oral submucous fibrosis by targeting Snail. Environ Toxicol. 2018 Apr;33(4):454-462. doi: 10.1002/tox.22531. Epub 2018 Jan 12. PMID: 29328529.


9: Wei KC, Chen RF, Chen YF, Lin CH. Hinokitiol suppresses growth of B16 melanoma by activating ERK/MKP3/proteosome pathway to downregulate survivin expression. Toxicol Appl Pharmacol. 2019 Mar 1;366:35-45. doi: 10.1016/j.taap.2019.01.015. Epub 2019 Jan 23. PMID: 30684529.


10: Wu YJ, Hsu WJ, Wu LH, Liou HP, Pangilinan CR, Tyan YC, Lee CH. Hinokitiol reduces tumor metastasis by inhibiting heparanase via extracellular signal- regulated kinase and protein kinase B pathway. Int J Med Sci. 2020 Feb 4;17(3):403-413. doi: 10.7150/ijms.41177. PMID: 32132875; PMCID: PMC7053356.


11: Tsao YT, Huang YF, Kuo CY, Lin YC, Chiang WC, Wang WK, Hsu CW, Lee CH. Hinokitiol Inhibits Melanogenesis via AKT/mTOR Signaling in B16F10 Mouse Melanoma Cells. Int J Mol Sci. 2016 Feb 18;17(2):248. doi: 10.3390/ijms17020248. PMID: 26901194; PMCID: PMC4783978.


12: Shih YH, Chang KW, Hsia SM, Yu CC, Fuh LJ, Chi TY, Shieh TM. In vitro antimicrobial and anticancer potential of hinokitiol against oral pathogens and oral cancer cell lines. Microbiol Res. 2013 Jun 12;168(5):254-62. doi: 10.1016/j.micres.2012.12.007. Epub 2013 Jan 11. PMID: 23312825.


13: Wang CC, Chen BK, Chen PH, Chen LC. Hinokitiol induces cell death and inhibits epidermal growth factor-induced cell migration and signaling pathways in human cervical adenocarcinoma. Taiwan J Obstet Gynecol. 2020 Sep;59(5):698-705. doi: 10.1016/j.tjog.2020.07.013. PMID: 32917321.


14: Chen X, Zhang X, Chen J, Yang Q, Yang L, Xu D, Zhang P, Wang X, Liu J. Hinokitiol copper complex inhibits proteasomal deubiquitination and induces paraptosis-like cell death in human cancer cells. Eur J Pharmacol. 2017 Nov 15;815:147-155. doi: 10.1016/j.ejphar.2017.09.003. Epub 2017 Sep 5. PMID: 28887042.


15: Huang CH, Lu SH, Chang CC, Thomas PA, Jayakumar T, Sheu JR. Hinokitiol, a tropolone derivative, inhibits mouse melanoma (B16-F10) cell migration and in vivo tumor formation. Eur J Pharmacol. 2015 Jan 5;746:148-57. doi: 10.1016/j.ejphar.2014.11.011. Epub 2014 Nov 20. PMID: 25449038.


16: Jayakumar T, Hsu WH, Yen TL, Luo JY, Kuo YC, Fong TH, Sheu JR. Hinokitiol, a natural tropolone derivative, offers neuroprotection from thromboembolic stroke in vivo. Evid Based Complement Alternat Med. 2013;2013:840487. doi: 10.1155/2013/840487. Epub 2013 Oct 27. PMID: 24285977; PMCID: PMC3826376.


17: Ni YJ, Huang ZN, Li HY, Lee CC, Tyan YC, Yang MH, Pangilinan CR, Wu LH, Chiang YC, Lee CH. Hinokitiol impedes tumor drug resistance by suppressing protein kinase B/mammalian targets of rapamycin axis. J Cancer. 2022 Mar 14;13(6):1725-1733. doi: 10.7150/jca.69449. PMID: 35399709; PMCID: PMC8990411.


18: Liu S, Yamauchi H. Hinokitiol, a metal chelator derived from natural plants, suppresses cell growth and disrupts androgen receptor signaling in prostate carcinoma cell lines. Biochem Biophys Res Commun. 2006 Dec 8;351(1):26-32. doi: 10.1016/j.bbrc.2006.09.166. Epub 2006 Oct 10. PMID: 17055455.


19: Shen YF, Ho CC, Shie MY, Wang K, Fang HY. Hinokitiol-Loaded Mesoporous Calcium Silicate Nanoparticles Induce Apoptotic Cell Death through Regulation of the Function of MDR1 in Lung Adenocarcinoma Cells. Materials (Basel). 2016 Apr 25;9(5):306. doi: 10.3390/ma9050306. PMID: 28773431; PMCID: PMC5503060.


20: Yang SC, Chen HY, Chuang WL, Wang HC, Hsieh CP, Huang YF. Different Cell Responses to Hinokitiol Treatment Result in Senescence or Apoptosis in Human Osteosarcoma Cell Lines. Int J Mol Sci. 2022 Jan 31;23(3):1632. doi: 10.3390/ijms23031632. PMID: 35163553; PMCID: PMC8835861.