Hinokitiol
Basic information
- CAS
499-44-5- Standard SMILES
CC(C)c1cccc(O)c(=O)c1- InChIKey
FUWUEFKEXZQKKA-UHFFFAOYSA-N- Molecular formula
- C10H12O2
- Average molar mass
- 164.2 g/mol
- Monoisotopic mass
- 164.08372962
Overview
Beta-thujaplicin is a monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Isolated from Thuja plicata and Chamaecyparis obtusa, it exhibits antimicrobial activities. It has a role as an antibacterial agent, an antineoplastic agent, an antifungal agent, an antiplasmodial drug and a plant metabolite. It is a monoterpenoid, an enol and a cyclic ketone. It derives from a hydride of a cyclohepta-1,3,5-triene.
Names & identifiers
- Preferred name
- Hinokitiol
- IUPAC
- 2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
- English name
- Hinokitiol
- Molecular formula
- C10H12O2
- Molecular weight
- 164.2
Names & synonyms
hinokitiol499-44-5beta-Thujaplicin4-Isopropyltropolone2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-one2-hydroxy-4-(propan-2-yl)cyclohepta-2,4,6-trien-1-oneU5335D6EBIDTXSID6043911NSC-18804CHEBI:10447
Show more names
β-thujaplicin2-HYDROXY-4-ISOPROPYLCYCLOHEPTA-2,4,6-TRIEN-1-ONE2-HYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIENEB-THUJAPLICINHinokitiol>
2-hydroxy-4-isopropyl-2,4,6-cycloheptatriene-1-onehydron;7-oxo-5-propan-2-ylcyclohepta-1,3,5-trien-1-olateRefChem:567983DTXCID4023911207-880-7Hinokitolbeta-ThujaplicineIsopropyltropolone
Database identifiers
- CAS
499-44-5- PubChem CID
- 3611
- DTXSID
DTXSID6043911
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 280
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
CosmeticsAntistatic; Hair conditioning
FragrancesFragrance Ingredient (2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-) -> IFRA transparency List
LogP1.82
Solubility1.2 mg/mL at 25 °C
Boiling Point140.00 °C. @ 10.00 mm Hg
Melting Point52 - 52.5 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 50 · 50-52 °C(lit.)
- Boiling point
- 140 °C10 · 140 °C10 mm Hg(lit.)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 106 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-
2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Toxicity Summary
The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of 2,4,6-cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- as described in this safety assessment. Data show that it is not genotoxic. The repeated dose, reproductive, and local respiratory toxicity endpoints were evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class I material, and the exposure to 2,4,6-cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- is below the TTC (0.03 mg/kg/day, 0.03 mg/kg/day, and 1.4 mg/day, respectively). The skin sensitization endpoint was completed using the Dermal Sensitization Threshold (DST) for reactive materials (64 μg/cm2); exposure is below the DST. Based on data, 2,4,6-cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- is a photoirritant but is not a concern under the current declared use levels. 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- has not been fully evaluated for photoallergenicity.
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems.
Cellular LocationsCytoplasm
Uses & manufacturing
Use Classification
Fragrance Ingredients
Cosmetics -> Antistatic; Hair conditioning
General Manufacturing Information2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-: ACTIVE
Applications
DescriptionHinokitiol (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.
UsesAntibacterial additive in foods, cosmetics, eye drops and toothpaste.
UsesHinokitiol 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.
Preparation methods
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Compound notes
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