Hinokitiol

Base Information

• Chemical Name: Hinokitiol
• CAS No.: 499-44-5
• Deprecated CAS: 772-41-8,333760-35-3,1411673-73-8,1411673-73-8,333760-35-3
• Molecular Formula: C10H12O2
• Molecular Weight: 164.204
• Hs Code.: 2914400090
• European Community (EC) Number: 207-880-7
• NSC Number: 18804
• UNII: U5335D6EBI
• DSSTox Substance ID: DTXSID6043911
• Nikkaji Number: J490.713B,J6.176J
• Wikipedia: Hinokitiol
• Wikidata: Q2705171
• RXCUI: 1312538
• Pharos Ligand ID: A9VGABS5346Y
• Metabolomics Workbench ID: 46872
• ChEMBL ID: CHEMBL48310
• Mol file: 499-44-5.mol

Synonyms:2-hydroxy-4-isopropyl- 2,4,6-cycloheptatriene-1-one;4-isopropyltropolone;beta-thujaplicin;beta-thujaplicin, sodium salt;hinokitiol

Chemical Property of Hinokitiol

Chemical Property:

• Vapor Pressure: 8.98E-05mmHg at 25°C
• Melting Point: 50-52 °C
• Refractive Index: 1.553
• Boiling Point: 303.4 °C at 760 mmHg
• PKA: 7.06±0.30(Predicted)
• Flash Point: 128.1 °C
• PSA: 37.30000
• Density: 1.127 g/cm³
• LogP: 1.87580
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 164.083729621
• Heavy Atom Count: 12
• Complexity: 280

Purity/Quality:

99% ^*data from raw suppliers

Hinokitiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1=CC(=O)C(=CC=C1)O
• Description: Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins.Hinokitiol is used in oral and skin care products,and is a food additive used in Japan.
• Uses: Antibacterial additive in foods, cosmetics, eye drops and toothpaste. Hinokitiol is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol has inhibitory effects on Chlamydia trachomatis and may be clinically useful as a topical drug.

Technology Process of Hinokitiol

There total 51 articles about Hinokitiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-amino-6-isopropyl-cycloheptatrienone (55076-49-8) → hinokitiol (499-44-5)

Guidance literature:

With potassium hydroxide;

DOI:10.1016/S0040-4039(00)74485-6

Reference yield: 98.0%

β-dolabrin (4570-11-0) → hinokitiol (499-44-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 22 ℃; for 6.5h; under 760 Torr;

Reference yield: 97.5%

isopropoxyboronic acid (52732-22-6) + 2-hydroxy-4-chloro-2,4,6-cycloheptatrien-1-one (698-48-6) → hinokitiol (499-44-5)

Guidance literature:

With potassium phosphate; In tetrahydrofuran; at 100 ℃; for 2h;

upstream raw materials:

β-isopropyltropolone

1-isopropyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

2-isopropylfuran

3-Isopropylcyclohepta-2,6-dienon

Downstream raw materials:

6-isopropyl-3-iodo-tropolone

3,5-dibromo-6-isopropyl-tropolone

α,α-bis(2-hydroxy-6-isopropyltropon-3-yl)-4-methoxytoluene

3-(α-ethoxy-4-methoxybenzyl)-6-isopropyltropolone

Refernces

• 1、 -. "Method for preparing hinokitiol". Paragraph 0083-0086. . Retrieved 2019/01/23.
• 2、 -. "Preparation method of beta-thujaplicine". Paragraph 0028; 0029; 0030; 0031; 0032; 0035; 0036. . Retrieved 2018/11/03.