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ヒノキチオール

Hinokitiol

HCID 3611
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
499-44-5
標準SMILES
CC(C)c1cccc(O)c(=O)c1
InChIKey
FUWUEFKEXZQKKA-UHFFFAOYSA-N
分子式
C10H12O2
平均分子量
164.2 g/mol
単同位体質量
164.08372962

概要

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.

名称と識別子

優先名称
Hinokitiol
IUPAC
2-hydroxy-6-propan-2-ylcyclohepta-2,4,6-trien-1-one
現地名
ヒノキチオール
英語名
Hinokitiol
分子式
C10H12O2
分子量
164.2

名称と別名

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
名称をさらに表示
ヒノキチオール4-イソプロピルトロポロン4-イソプロピル-2-ヒドロキシ-2,4,6-シクロヘプタトリエン-1-オン2-ヒドロキシ-4-イソプロピルシクロヘプタン-2,4,6-トリエン-1-オンβ-ツヤプリシン2-ヒドロキシ-4-イソプロピル-2,4,6-シクロヘプタトリエン-1-オンヒノキトールβ-ツジャプリシン2-ヒドロキシ-4-(1-メチルエチル)-2,4,6-シクロヘプタトリエン-1-オンヒノキチオ-ルツヤプリシン, BETA-ツヤプリシン, BETA-(HINOKヒノキチオール4-イソプロピルトロポロン (ヒノキチオール)2-ヒドロキシ-4-(プロパン-2-イル)シクロヘプタ-2,4,6-トリエン-1-オン2-ヒドロキシ-4-イソプロピルシクロヘプタ-2,4,6-トリエン-1-オン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

データベース識別子

CAS
499-44-5
PubChem CID
3611
DTXSID
DTXSID6043911
ChEMBL
CHEMBL48310
ChEBI
CHEBI:10447
UNII
U5335D6EBI
EC Number
207-880-7
Nikkaji
J490.713B、J6.176J

物性

構造計算による物性

XLogP
2.1
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
12
形式電荷
0
複雑度
280

実験および物理化学的性質

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

物理化学的性質

融点
50 · 50-52 °C(lit.)
沸点
140 °C10 · 140 °C10 mm Hg(lit.)
比重(密度)
1.0041 · 1.0041 (rough estimate)
屈折率
1.519 · 1.5190 (estimate)
貯蔵温度
Sealed in dry,Room Temperature
溶解性
DMSO (最大 25mg/ml) またはエタノール (最大 25mg/ml) に可溶。
酸解離定数(Pka)
7.06 · 7.06±0.30(Predicted)
外見
個体
色
白い
臭い (Odor)
100 %で。フェノール系木質苔状 · 100.00%で。フェノール系木質苔状
においのタイプ
木質の
Merck
14 · 14,9390
安定性
-20 °C · -20°C の DMSO またはエタノール溶液で最大 4 か月間保存できます。
化粧品成分の機能
ヘアコンディショニング帯電防止
LogP
1.137 · 1.137 (est)
CAS データベース
499 · 499-44-5(CAS DataBase Reference)
NISTの化学物質情報
2 · 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-(499-44-5)
EPAの化学物質情報
2 · 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- (499-44-5)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 2 件

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%)

毒性情報

Toxicity Summary · 1 件

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.

Environmental Fate/Exposure Summary · 1 件

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. For the hazard assessment based on the screening data, 2,4,6-cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)- was found not to be Persistent, Bioaccumulative, and Toxic (PBT) as per the International Fragrance Association (IFRA) Environmental Standards, and its risk quotients, based on its current volume of use (VoU) in Europe and North America (i.e., Predicted Environmental Concentration/Predicted No Effect Concentration [PEC/PNEC]), are less than 1.

安全データ

wgk
3
tsca
TSCA listed
rtecs
GU4200000
hs_code
2914290090
risk_code
22
化審法
(3)-2396, (9)-1526
hazard_code
Xn
safety_code
36

化学と産業

薬理情報

MeSH Pharmacological Classification · 3 件

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

用途と製造

Use Classification · 2 件

Fragrance Ingredients

Cosmetics -> Antistatic; Hair conditioning

General Manufacturing Information2,4,6-Cycloheptatrien-1-one, 2-hydroxy-4-(1-methylethyl)-: ACTIVE
応用分野 · 4 件

解説ヒノキチオール,4-イソプロピルトロポロンともいう.タイワンヒノキChamaecyparis taiwanensisの精油の酸性成分から単離されたので,この名称が与えられたが,ヒバなどの精油中にも見いだされている.無色の柱状結晶.融点52~53 ℃,沸点140 ℃(1.3 kPa).d2041.094.n20D1.607.pKa 7.21.λmax 236,322,353 nm(log ε 4.37,3.72,3.66).鉄(Ⅲ)錯体は暗赤色の結晶.融点250~251 ℃.銅(Ⅱ)錯体は緑色の結晶.融点177~178 ℃.親電子試薬は3,5および7位に反応して種々の置換体を与える.

用途医薬品原料、防腐剤の研究用。

説明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.

使用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.

上流・下流製品情報

上流原料

1,3-Cycloheptadiene,1-methoxy-6-(1-methylethyl)-(9CI)Boric acid, mono(1-methylethyl) ester2,4,6-Cycloheptatrien-1-one, 4-chloro-2-hydroxy-2-ヒドロキシ-4-イソプロペニル-2,4,6-シクロヘプタトリエン-1-オン3-Cycloheptene-1,2-dione,6-(1-methylethyl)-,(6S)-(9CI)2,4,6-Cycloheptatrien-1-one, 4-bromo-2-hydroxy-2,4,6-Cycloheptatrien-1-one,2-amino-6-(1-methylethyl)-(9CI)Cycloheptanone, 3-(1-methylethyl)-1,3,5-Cycloheptatriene, 1-methoxy-

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補足説明

定義本品は、次の化学式で表される環式アルコールである。

定義ChEBI: 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.

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