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クミンアルデヒド

Cuminaldehyde

HCID 326
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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
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基本情報

CAS
122-03-2
標準SMILES
CC(C)c1ccc(C=O)cc1
InChIKey
WTWBUQJHJGUZCY-UHFFFAOYSA-N
分子式
C10H12O
平均分子量
148.2 g/mol
単同位体質量
148.088815

概要

Cuminaldehyde is a member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities. It has a role as an insecticide, a volatile oil component and a plant metabolite. It derives from a hydride of a cumene.

名称と識別子

優先名称
Cuminaldehyde
IUPAC
4-propan-2-ylbenzaldehyde
現地名
クミンアルデヒド
英語名
Cuminaldehyde
分子式
C10H12O
分子量
148.2

名称と別名

4-isopropylbenzaldehydecuminaldehyde122-03-2cuminic aldehydecumaldehydecuminalp-cumic aldehydeCumic aldehydeCuminyl aldehydeBenzaldehyde, 4-(1-methylethyl)-P-ISOPROPYLBENZALDEHYDEp-Isopropylbenzenecarboxaldehyde
名称をさらに表示
クミンアルデヒドクマアルデヒドクミナールp-イソプロピルベンズアルデヒド4-(1-メチルエチル)-ベンズアルデヒド4-(1-メチルエチル)ベンズアルデヒドクミニルアルデヒドクムアルデヒド4-イソプロピルベンズアルデヒドp-クミンアルデヒドｐ-ｉｓｏ-プロピルベンズアルデヒドOIL4-(1-methylethyl)-BenzaldehydeFEMA 2341ISOPROPYLBENZALDEHYDE
4-(1-Methylethyl)benzaldehydeP-isopropyl benzaldehyde4-(Propan-2-Yl)Benzaldehyde4-propan-2-ylbenzaldehydeFEMA No. 2341DTXSID9021974O0893NC35FNSC-4886

データベース識別子

CAS
122-03-2
PubChem CID
326
DTXSID
DTXSID9021974
ChEMBL
CHEMBL161577
ChEBI
CHEBI:28671
UNII
O0893NC35F
EC Number
204-516-9
Nikkaji
J5.347C

物性

構造計算による物性

XLogP
2.7
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
2
重原子数
11
形式電荷
0
複雑度
121

実験および物理化学的性質

Chemical ClassesOther Classes -> Benzaldehydes
SpringerMaterials PropertiesCoriolis coupling
Fragrances · 2 件

Fragrance substance (Cuminaldehyde) -> IFRA amendment 49

Fragrance Ingredient (Cuminic aldehyde) -> IFRA transparency List

LogP3.170
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.973-0.981
Flavoring AgentsEU Flavoring substances
Solubility · 3 件

282 mg/L @ 20 °C (exp)

insoluble in water; soluble in organic solvents, oils

miscible at room temperature (in ethanol)

Boiling Point · 2 件

235.5 °C

235-236 °C

Refractive Index1.527-1.534
Physical Description · 3 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 · 6 件

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1792) of reports.

Warning

H302 (99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

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

Aggregated GHS information provided per 1792 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory Information · 5 件

Chemical: Benzaldehyde, 4-(1-methylethyl)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzaldehyde, 4-(1-methylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzaldehyde, 4-(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: 4-isopropylbenzaldehyde (EC: 204-516-9)

4-Isopropylbenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Causes somnolence, ulceration or bleeding from the stomach, and other liver changes in oral lethal-dose studies of rats; [RTECS] Fragrance ingredient with positive human patch test results (3 of 179 patients), but insufficient data to classify as established contact allergen in humans; [EC: SCCS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS] Search for (122-03-2[EC/RN Number]) AND (allergic OR dermatitis OR sensitizer OR sensitization): no results; [PubMed]

Hazard Classes and Categories · 2 件

Acute Tox. 4 (99.9%)

Acute toxicity (Oral) - Category 4

化学と産業

薬理情報

Cellular LocationsExtracellular

用途と製造

UsesOccurs naturally in eucalyptus, myrrh, cumin, and other oils; Used in perfumes; [Merck Index] Used as a flavoring agent; [FDA] Used to make large scale and fine chemicals; [ECHA REACH Registrations]
U.S. Production2020: 8,816 lb
IFRA Fragrance Standards · 6 件

Cuminaldehyde

Benzaldehyde, 4-(1-methylethyl)-; Cumaldehyde; Cuminal; Cuminic aldehyde; 4-Isopropylbenzaldehyde; p-Isopropylbenzaldehyde; 4-Isopropylbenzenecarboxaldehyde

IFRA_STD_024.pdf

49

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Restriction: This material should be used only in the limited quantity as stated in the Standard

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 InformationBenzaldehyde, 4-(1-methylethyl)-: ACTIVE
Restriction Limits in the Finished Product (%) · 6 件

0.085 [Products applied to the lips]

0.025 [Products applied to the axillae]

0.51 [Products applied to the face/body using fingertips]

0.47 [Products related to fine fragrances]

0.12 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.12 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]

関連反応

81 件
反応記録を作成
HRID 53354 の反応式
HRID 53354反応物としてuspto-grants-1997_04
HRID 100247 の反応式
HRID 100247反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 118071 の反応式
HRID 118071反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 133609 の反応式
HRID 133609反応物としてuspto-grants-2008_06
HRID 144335 の反応式
HRID 144335反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 167004 の反応式
HRID 167004反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 173867 の反応式
HRID 173867反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 193232 の反応式
HRID 193232反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
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化合物ノート

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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

Colorless to yellowish liquid with a strong odor; [Merck Index] Colorless liquid; [Alfa Aesar MSDS]

Liquid

colourless to pale yellow liquid with a strong, pungent, spicy, green, herbaceous odour

物理化学的性質

融点
97 °C · 97 °C
沸点
235 · 235-236 °C(lit.)
比重(密度)
0.977 g/mL · 0.977 g/mL at 25 °C(lit.)
屈折率
20 · n20/D 1.529(lit.)
FEMA
2341 · 2341 | CUMINALDEHYDE
闪点
200 °F · 200 °F
貯蔵温度
2 · Inert atmosphere,2-8°C
溶解性
1 mL/4ML · エタノール：可溶1mL/4ML 無色透明(70%)
外見
液体
色
無色透明～黄色
臭い (Odor)
10 %。スパイシークミングリーンハーブ · ジプロピレングリコール中10.00%。スパイシークミングリーンハーブ
においのタイプ
辛い
由来生物
synthetic
水溶解度
不溶性
Merck
14 · 14,2621
JECFA Number
868 · 868
BRN
636547 · 636547
Dielectric constant
11 · 11.0(15℃)
化粧品成分の機能
香料
InChI
1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3
InChIKey
WTWBUQJHJGUZCY-UHFFFAOYSA-N
SMILES
[H]C(=O)c1ccc(cc1)C(C)C
LogP
3.17 · 3.17
CAS データベース
122 · 122-03-2(CAS DataBase Reference)
NISTの化学物質情報
4 · Benzaldehyde, 4-(1-methylethyl)-(122-03-2)
EPAの化学物質情報
Cuminaldehyde (122-03-2)

化学的性質

化学的特性Cuminaldehyde has a strong, pungent, cumin-like odor and similar taste.

安全データ

wgk
2
tsca
TSCA listed
rtecs
CU7000000
毒性
LD50 orally in rats: 1390 mg/kg (Jenner)
hs_code
29122900
risk_code
22-36/37/38
化審法
(3)-1144, (3)-2663
消防法
危-4-3-III
hazard_code
Xn,Xi
safety_code
26-36-37/39
Hazard Classifications
Acute Tox. 4 Oral
ストレージクラス
10 - Combustible liquids
応用分野 · 5 件

用途スパイスフレーバーな どの食品香料およびシクラメンアルデヒドの合成原料

用途香料材料、有機合成原料。

天然物の起源Reported in a large number of essential oils, cumin, Acacia farnesiana, cinnamon, bitter orange, Mexican lime, Eucalyptus globulus, rue, boldus, Artemisia hausiliensis and others. Also reported in lemon and mandarin peel oil, cinnamon bark, anise, clove bud, cumin seed, turmeric, parsley, calabash nutmeg (Monodora myristica Dunal), angelica root, thyme, beef, brandy, grape and mastic gum fruit oil.

使用Cuminaldehyde is a flavoring agent that is a liquid, colorless to yellow in appearance, with a strong pungent odor resembling cumin oil. It is insoluble in water and soluble in alcohol and ether. It is obtained from cumin oil. It is also termed p-, cumaldehyde, and cuminal.

一般的な説明Cuminaldehyde is a constituent of cumin oil that exhibits strong antifungal and antibacterial activities.

調製方法 · 2 件

製造方法From p-isopropylbenzyl chloride and hexamethylenetetramine (Arctander, 1969).

純化方法A likely impurity is the benzoic acid. Check the IR for the presence of OH from CO2H, and the CO frequencies. If the acid is present, then dissolve the aldehyde in Et2O, wash it with 10% NaHCO3 until effervescence ceases, then with brine, dry over CaCl2, evaporate and distil the residual oil, preferably under vacuum. It is almost insoluble in H2O, but soluble in EtOH and Et2O. The thiosemicarbazone has m 147o after recrystallisation from aqueous EtOH, MeOH or *C6H6. [Crounse J Am Chem Soc 71 1263 1949, Bernstein et al. J Am Chem Soc 73 906 1951, Gensler & Berman J Am Chem Soc 80 4949 1958, Beilstein 7 H 318, 7 II 347, 7 III 1095, 7 IV 723.]

上流・下流製品情報

上流原料

ヘキサメチレンテトラミンp-シメン[acetyloxy-(4-propan-2-ylphenyl)methyl] acetateBenzene, 1-(1-methylethyl)-4-[[(trimethylsilyl)oxy]methyl]-2-PROPYLZINC BROMIDE 溶液4-イソプロピルスチレン4-イソプロピルベンジルアミン4-イソプロピルベンジル クロリド4-イソプロピルベンジルアルコール4-ブロモベンズアルデヒドクメン

下流製品

3-(4-イソプロピルフェニル)イソブチルアルデヒド4-イソプロピルベンジルブロミド1-(2-Hydroxyphenyl)-3-(4-isopropylphenyl)prop-2-en-1-one4-イソプロピルベンズアルデヒドセミカルバゾン

補足説明

定義ChEBI: A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.