ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /化合物

カルバクロール

Carvacrol

HCID 10364
ノートを作成反応を作成見積依頼を出す
印刷プレビュー
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
499-75-2
標準SMILES
Cc1ccc(C(C)C)cc1O
InChIKey
RECUKUPTGUEGMW-UHFFFAOYSA-N
分子式
C10H14O
平均分子量
150.22 g/mol
単同位体質量
150.10446507

概要

Carvacrol is a phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). It has a role as a TRPA1 channel agonist, a volatile oil component, an antimicrobial agent, an agrochemical and a flavouring agent. It is a p-menthane monoterpenoid, a member of phenols and a botanical anti-fungal agent. It derives from a hydride of a p-cymene.

名称と識別子

優先名称
Carvacrol
IUPAC
2-methyl-5-propan-2-ylphenol
現地名
カルバクロール
英語名
Carvacrol
分子式
C10H14O
分子量
150.22

名称と別名

CARVACROL5-Isopropyl-2-methylphenol499-75-2Isopropyl-o-cresolAntioxine2-p-Cymenol5-Isopropyl-o-cresol2-Hydroxy-p-cymenePhenol, 2-methyl-5-(1-methylethyl)-Karvakrolp-Cymen-2-ol2-Methyl-5-isopropylphenol
名称をさらに表示
カルバクロール2-メチル-5-イソプロピルフェノールアンチオキシン2-p-シメノール5-イソプロピル-2-メチルフェノール3-イソプロピル-6-メチルフェノール5-イソプロピル-o-クレゾールイソチモール6-メチル-3-(1-メチルエチル)フェノール2-ヒドロキシ-p-シメン2-メチル-5-(1-メチルエチル)フェノール2-メチル-5-(プロパン-2-イル)フェノールカルバクロール(イソチモール)ピオゾールイソプロピル-ｏ-クレゾールo-ThymolISOTHYMOLCymenolFEMA 22452-hydroxy-p-cymen
2-methyl-5-propan-2-ylphenol3-Isopropyl-6-methylphenolp-Cymene, 2-hydroxy-1-Hydroxy-2-methyl-5-isopropylbenzeneFEMA No. 2245Phenol, 5-isopropyl-2-methyl-1-Methyl-2-hydroxy-4-isopropylbenzeneDENTOL

物性

構造計算による物性

XLogP
3.1
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
1
重原子数
11
形式電荷
0
複雑度
120

実験および物理化学的性質

Chemical ClassesBiological Agents -> Plant Oils and Extracts
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
CosmeticsCosmetic ingredients (Carvacrol) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials PropertiesDensity
Fragrances · 2 件

Fragrance Ingredient (Carvacrol) -> IFRA transparency List

Fragrance

Pesticides · 2 件

Other Treatment

Active substance -> EU Pesticides database: Pending

LogP · 2 件

3.49

3.49

Odor · 2 件

THYMOL ODOR

MEDICINAL SMOKE ODOR

TasteEXCELLENT SMOKE TASTE, @ 1-5 PPM
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 件

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 · 5 件

This chemical does not meet GHS hazard criteria for 0.1% (2 of 1828) of reports.

Warning

H302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1828 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 5 件

Chemical: Phenol, 2-methyl-5-(1-methylethyl)-

Regulation (EC) No 1831/2003 (amended)

Phenol, 2-methyl-5-(1-methylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2-methyl-5-(1-methylethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Carvacrol (EC: 207-889-6)

5-Isopropyl-2-methylphenol: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryEmergency treatment: Irritants; [HSDB] Causes severe irritation on rabbit skin; Causes somnolence and convulsions at lethal doses; [RTECS] Safe when used as a flavoring agent in food; [JECFA]
FDA Requirements · 2 件

172.515

121.1164; LIMITATIONS: SYNTHETIC FLAVOR.

Special Reports · 1 件

REVIEW WITH 42 REF ON CARVACROL INCL TOXICITY, IRRITATION, SENSITIZATION, METAB, PERCUTANEOUS ABSORPTION, PHARMACOLOGY, CYTOTOXICITY, CHEMOTHERAPY, & EFFECT ON ISOLATED TISSUES & ORGANELLES.[OPDYKE DL J; MONOGRAPH ON FRAGRANCE RAW MATERIALS. CARVACROL; FOOD COSMET TOXICOL 17(ISS SUPPL) 743 (1979)]

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

/WHEN FED TO RABBITS,/ THE SUBSTITUTED MONOPHENOLS, THYMOL & CARVACROL, WHICH OCCUR IN ESSENTIAL OILS OF PLANTS...ARE...CONJUGATED WITH GLUCURONIC ACID & SULFATE.

CARVACROL IS METABOLIZED BY CONJUGATION WITH GLUCURONIC ACID & SULFATE.

Carvacrol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(2-methyl-5-propan-2-ylphenoxy)oxane-2-carboxylic acid and (2-methyl-5-propan-2-ylphenyl) hydrogen sulfate.

Absorption, Distribution and Excretion · 2 件

CARVACROL APPEARS TO BE SLOWLY ABSORBED FROM INTESTINE IN RABBIT, SINCE 22 HR AFTER ADMIN OF 1.5 G, SOME 30% WAS STILL IN GASTRO-INTESTINAL TRACT, ABOUT 25% OF DOSE HAVING BEEN EXCRETED IN URINE.

CARVACROL APPLIED TO INTACT SHAVED ABDOMINAL SKIN OF MOUSE WAS NOT ABSORBED WITHIN 2 HR.

Cellular LocationsExtracellular

用途と製造

Uses · 6 件

CIR ingredient: Carvacrol

Found in oil of origanum, thyme, marjoram, and summer savory; Used as a disinfectant, fungicide, and anthelmintic (nematodes); Also used in organic syntheses and in perfumes and flavorings; [Hawley] Origanum oil is about 60% carvacrol; [HSDB]

Using Disinfectants or Biocides [Category: Clean]

DISINFECTANT; IN ORGANIC SYNTHESES

MEDICATION: ANTIFUNGAL; ANTHELMINTIC AGENT

PERFUMES; FLAVORING

U.S. Production2023: 2,500 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 2 件

FROM P-CYMENE BY SULFONATION & SUBSEQUENT ALKALI FUSION. HIXSON & MCKEE, CHEM ZENTR, II: 851, 1919; GIBBS & PHILLIPS, J IND ENG CHEM, 12: 145, 1920.

関連反応

13 件
反応記録を作成
HRID 80823 の反応式
HRID 80823生成物としてuspto-grants-2014_09
HRID 251647 の反応式
HRID 251647反応物としてuspto-grants-2011_01
HRID 273664 の反応式
HRID 273664生成物としてuspto-grants-1995_02
HRID 296675 の反応式
HRID 296675反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 606305 の反応式
HRID 606305反応物としてuspto-grants-2011_03
HRID 1091938 の反応式
HRID 1091938反応物としてuspto-grants-2012_03
HRID 1392681 の反応式
HRID 1392681反応物としてuspto-grants-2008_03
HRID 1455756 の反応式
HRID 1455756反応物としてuspto-grants-2009_01
1 / 2 ページ

化合物ノート

読み込み中…

このページの内容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
その他の操作
ノートを作成反応を作成見積依頼を出す

データベース識別子

CAS
499-75-2
PubChem CID
10364
DTXSID
DTXSID6042074
ChEMBL
CHEMBL281202
ChEBI
CHEBI:3440
UNII
9B1J4V995Q
EC Number
207-889-6
Nikkaji
J6.180H

0.976 @ 20 °C/4 °C

0.974-0.979

Flavoring AgentsEU Flavoring substances

物理化学的性質

融点
3 · 3-4 °C(lit.)
沸点
236 · 236-237 °C(lit.)
比重(密度)
0.976 g/mL · 0.976 g/mL at 20 °C(lit.)
蒸気圧
3.09 · 3.09-6.664Pa at 25℃
FEMA
2245 · 2245 | CARVACROL
屈折率
20 · n20/D 1.522(lit.)
闪点
224 °F · 224 °F
貯蔵温度
-20 °C · -20°C
溶解性
1.25 g/リットル · 1.25g/リットル
酸解離定数(Pka)
10.38 · 10.38±0.10(Predicted)
外見
Liquid
色
Colorless to Light orange to Yellow
臭い (Odor)
100 %で。スパイス · 100.00%で。スパイス ウッディ カンファー チモール
においのタイプ
辛い
由来生物
synthetic
水溶解度
不溶性
Merck
14 · 14,1872
JECFA Number
710 · 710
BRN
1860514 · 1860514
Henry's Law Constant
1.5 · 1.5×100 mol/(m3Pa) at 25℃, Martins et al. (2017)
安定性
安定。可燃性。強塩基、強酸化剤とは相容れない。
主な用途
洗浄剤化粧品フレーバーそして香料食品および飲料パーソナルケア
化粧品成分の機能
香料
InChI
1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3
InChIKey
RECUKUPTGUEGMW-UHFFFAOYSA-N
SMILES
CC(C)c1ccc(C)c(O)c1
LogP
3.33 · 3.33-3.49
CAS データベース
499 · 499-75-2(CAS DataBase Reference)
NISTの化学物質情報
2 · Phenol, 2-methyl-5-(1-methylethyl)-(499-75-2)
EPAの化学物質情報
Isopropyl-o-cresol (499-75-2)
化学的性質 · 2 件

化学的特性カルバクロールは強力な抗菌性を持つフェノール類の一種でその化学式はC10H14Oですこの化合物はオレガノタイムペパーミントマウンテンサボリーなどの植物に自然に存在しこれらの植物が持つ独特の香りの主要成分の一つですカルバクロールは食品添加物防腐剤そして医薬品としての利用が広がっていますまた自然界に存在する抗菌性化合物としてその効果と利用可能性について多くの研究がなされています

化学的特性Carvacrol has a characteristic pungent, warm odor. The commercial product consists of a mixture of isomers differing because of the position of the isopropyl radical. The odor characteristics differ between the technical (lower grade) and pure (higher grade) commercial products.

Hazard Classes and CategoriesAcute Tox. 4 (99.8%)

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary · 2 件

The CIR Expert panel concludes Sodium p-Chloro-m-Cresol, p-Chloro-m-Cresol, Chlorothymol, m-Cresol, o-Cresol, Isopropyl Cresols, Thymol, o-Cymen-5-ol, Cavacrol are safe at concentrations up to 0.5% in cosmetics; however, the available data are insufficient to support the safety of p-Cresol and Mixed Cresols for use in cosmetic products.

Safe for use in cosmetics, with qualifications

Natural Pollution Sources · 2 件

FOUND IN OIL OF ORIGANUM, THYME, MARJORAM, SUMMER SAVORY...

OCCURS IN BARK OIL OF THUJA ARTICULATA, CAMPHOR OIL, IN OILS OF MONARDA CITRIODORA & MONARDA FISTULOSA, IN SOME SPECIES OF SATUREJA, IN OIL OF VARIOUS SPECIES OF ORIGANUM, THYME, THYMBRA SPICATA L, IN SEED OIL OF PTYCHOTIS AJOWAN DC, & OTHERS.

Human Toxicity Excerpts · 2 件

TECHNICAL GRADE (1.0 & 0.1% IN ETHANOL) PRODUCED POS PATCH TESTS IN PT WITH ACUTE DERMATITIS OF FACE, BUT NO POS RESPONSES IN CONTROL SUBJECTS. TESTED @ 4% IN PETROLATUM, IT PRODUCED NO IRRITATION AFTER 48-HR.

CARVACROL SHOWED MODERATE CYTOTOXIC EFFECTS IN HELA CELLS.

Non-Human Toxicity Excerpts · 5 件

SOMEWHAT MORE TOXIC THAN THYMOL IN RATS & RABBITS.

EVALUATED FOR MUTAGENIC EFFECTS TO 5 STRAINS OF SALMONELLA TYPHIMURIUM EMPLOYING PROCEDURES DESCRIBED BY AMES, ISOTHYMOL HAD PRONOUNCED MUTAGENICITY.

CARVACROL APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS SEVERELY IRRITATING.

WHEN MIXT OF 93% CARVACROL & 7% THYMOL IN ARACHIS OIL WAS ADMIN BY GASTRIC INTUBATION TO CFE STRAIN RATS IN SINGLE DOSE OF 1.5 MMOL/KG, SLIGHT INCR IN PRODUCTION OF LIVER BIPHENYL-4-HYDROXYLASE WAS NOTED.

CARVACROL SHOWED PAPAVERINE-LIKE ANTISPASMODIC ACTION ON ISOLATED SMALL INTESTINE OF MOUSE. ADDED TO BOVINE SEMINAL VESICLE MICROSOMES @ 4.1 UG/ML, IT INHIBITED THE IN VITRO FORMATION OF PROSTAGLANDIN E1 BY 50%.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

法規制情報

FDA Requirements · 2 件

172.515

121.1164; LIMITATIONS: SYNTHETIC FLAVOR.

安全データ

wgk
3
tsca
TSCA listed
rtecs
FI1225000
ridadr
UN 3265 8/PG 3
毒性
LD orally in rabbits: 100 mg/kg (Kochmann)
hs_code
29071990
risk_code
22-34
化審法
(4)-57
消防法
危-4-3-III
hazard_code
C
safety_code
26-36/37/39-45
hazard_class
8
packing_group
III
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Skin Corr. 1B
ストレージクラス
8A - Combustible corrosive hazardous materials
有毒物質データの
499-75-2(Hazardous Substances Data)

...BY CHLORINATION OF ALPHA-PINENE WITH TERT-BUTYL HYPOCHLORITE: RITTER, GINSBURG, J AM CHEM SOC 72, 2381 (1950); FROM 2-BROMO-P-CYMOL: STRUBELL, BAUMGARTEL, ARCH PHARM 291, 66 (1958).

Formulations/Preparations · 2 件

THE COMMERCIAL PRODUCT CONSISTS OF A MIXTURE OF ISOMERS DIFFERING BECAUSE OF THE POSITION OF THE ISOPROPYL RADICAL. THE TECHNICAL & PURE QUALITY ARE DIFFERENT BECAUSE OF THE ODOR CHARACTERISTICS.

THE MAIN CONSTITUENT/OF ORIGANUM OIL/IS CARVACROL (ca 60%)

Household ProductsInformation on 1 consumer products that contain Carvacrol in the following categories is provided:
Use Classification · 6 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 5 件

Not Known or Reasonably Ascertainable

Phenol, 2-methyl-5-(1-methylethyl)-: ACTIVE

FLAVORS USEFUL IN: SMOKE FLAVORS, SPICE, MEAT FLAVORS.

REPORTED USES: /IN/ NON-ALCOHOLIC BEVERAGES 26 PPM; ICE CREAM, ICES, ETC 34 PPM; CANDY 92 PPM; BAKED GOODS 120 PPM; CONDIMENTS 37 PPM.

FEMA NUMBER 2245

応用分野 · 5 件

解説カルバクロールは，精油成分の一つ．オリガヌム油やしょうのう油などに含まれ，広く植物界に存在する．フェノール様の特臭を有する液体。空気または日光により着色する．融点0.5～1 ℃，沸点237 ℃．d20 0.976．n20D 1.5205～1.5240．フェノール様の臭気があり，水に不溶，エタノールやエーテルなどに可溶．せっけんの香料，香料として使われる食品添加物, 薬用化粧品の製造などに用いられる．森北出版「化学辞典（第2版）

用途強力な防腐剤、殺菌剤として医薬またはロコウ剤の製造その他に広く用いられる。

天然物の起源Reported found in cumin seed, thyme, oregano, calamus, lovage, myrtle and lemon balm.

使用Carvacrol is a flavoring agent that is a colorless to pale yellow liquid. it has a spicy and pungent odor, resembling thymol. it is insoluble in water and soluble in alcohol and ether. it is a mixture of the isomeric carvacrols (isopropyl o-creols), and is obtained by chemical synthesis. it is also an ingredient of savory, a fragrant herb in nature.

一般的な説明Produced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.

調製方法

製造方法From p-cymene by sulfonation and subsequent alkali fusion.

上流・下流製品情報

上流原料

Eucalyptus Citriodara OilチモールBicyclo[4.1.0]hept-3-en-2-one, 4,7,7-trimethyl-Bicyclo[4.1.0]hept-3-en-2-one, 3,7,7-trimethyl-2,4-Cycloheptadien-1-one, 3,6,6-trimethyl-Bicyclo[4.1.0]hept-4-en-3-one, 4,7,7-trimethyl-2,6,6-トリメチル-2,4-シクロヘプタジエン-1-オン3-メチル-5-(1-メチルエチル)フェノール

下流製品

アセトアミド2-(5-Isopropyl-2-methyl-phenoxy)-ethylamine

補足説明

定義ChEBI: A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).