Citronellic acid (HCID 10402)

概要

Citronellic acid is a monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7. It has a role as a flavouring agent and a plant metabolite. It is a monoterpenoid, a monounsaturated fatty acid and a medium-chain fatty acid. It is functionally related to a citronellal.

名称と識別子

優先名称: Citronellic acid
IUPAC: 3,7-dimethyloct-6-enoic acid
現地名: シトロネル酸
英語名: CITRONELLIC ACID
分子式: C10H18O2
分子量: 170.25

名称と別名

Citronellic acid3,7-dimethyloct-6-enoic acid502-47-63,7-Dimethyl-6-octenoic acidRhodinolic acidRhodinic Acid6-OCTENOIC ACID, 3,7-DIMETHYL-FEMA No. 3142DTXSID10471061JJT408R87DTXCID9027106CHEBI:80507

名称をさらに表示

シトロネル酸3,7-ジメチル-6-オクテン酸(±)-シトロネル酸3，7-ジメチルオクタ-6-エン酸FEMA 3142TIMTEC-BB SBB006596Citronellic acid 98%Citronellic Acid >(+/-)-CITRONELLIC ACID

RefChem:577476207-939-7Citronellate57030-77-0MFCD00002728EINECS 207-939-7BRN 1722960Callitrol

データベース識別子

CAS: 502-47-6
PubChem CID: 10402
DTXSID: DTXSID1047106
ChEMBL: CHEMBL2288023
ChEBI: CHEBI:80507
UNII: 1JJT408R87
EC Number: 207-939-7
Nikkaji: J11.776E

物性

構造計算による物性

XLogP: 3
極性表面積: 37.3 Å²
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: 5
重原子数: 12
形式電荷: 0
複雑度: 167

実験および物理化学的性質

Chemical ClassesOther Classes -> Organic Acids

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Branched fatty acids [FA0102]

FragrancesFragrance Ingredient (3,7-Dimethyl-6-octenoic acid) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density0.920-0.926 (20 °C)

Flavoring AgentsEU Flavoring substances

物理化学的性質

沸点: 121 · 121-122 °C1 mm Hg(lit.)
比重(密度): 0.923 g/mL · 0.923 g/mL at 25 °C(lit.)
FEMA: 3142 · 3142 | 3,7-DIMETHYL-6-OCTENOIC ACID
屈折率: 20 · n20/D 1.454(lit.)
闪点: 230 °F · >230 °F
貯蔵温度: 2 · Storage temp. 2-8°C
溶解性: Almost insoluble in water, soluble in tslcohol and oils.
酸解離定数(Pka): 4.78 · 4.78±0.10(Predicted)
外見: clear liquid
色: Colorless to Light yellow
臭い (Odor): 10 %。緑の草のようなスモーキーな脂肪の花 · ジプロピレングリコール中10.00%。緑の草のようなスモーキーな脂肪の花
においのタイプ: 緑
由来生物: synthetic
水溶解度: 水に不溶。
JECFA Number: 1221 · 1221
化粧品成分の機能: 抗脂漏性抗菌剤香料
InChI: 1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)
InChIKey: GJWSUKYXUMVMGX-UHFFFAOYSA-N
SMILES: CC(CC\C=C(\C)C)CC(O)=O
LogP: 3.35 · 3.35
CAS データベース: 502 · 502-47-6(CAS DataBase Reference)
EPAの化学物質情報: 6 · 6-Octenoic acid, 3,7-dimethyl- (502-47-6)

化学的性質

化学的特性Citronellic acid has a green-grassy odor.

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H311 (> 99.9%): Toxic in contact with skin [Danger Acute toxicity, dermal]

P262, P264, P270, P280, P302+P352, P316, P321, P361+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1635 reports by companies from 6 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 3 件

Chemical: 6-Octenoic acid, 3,7-dimethyl-

Regulation (EC) No 1831/2003 (amended)

6-Octenoic acid, 3,7-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA moderate skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin irritant; Toxic by skin absorption; [Sigma-Aldrich MSDS] See Citronellol.

Hazard Classes and CategoriesAcute Tox. 3 (> 99.9%)

安全データ

wgk: 3
tsca: TSCA listed
rtecs: RH3230000
ridadr: UN 2810 6.1/PG 3
hs_code: 29161995
risk_code: 21-38
化審法: (2)-609
消防法: 危-4-3-III
hazard_code: Xn
safety_code: 36/37
hazard_class: 6.1
packing_group: III
Hazard Classifications: Acute Tox. 3 DermalSkin Irrit. 2
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

Cellular LocationsExtracellular

用途と製造

UsesUsed as a flavoring agent; [FDA]

Use Classification · 4 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information6-Octenoic acid, 3,7-dimethyl-: ACTIVE

応用分野 · 2 件

天然物の起源The d-form is reportedly a constituent of Java citronella, geranium, Borosma pulchellum, Xanthoxylum piperitum, bitter-orange leaves, lemongrass, Calytrix virgata and Calytrix tetragona leaves; the l-form has been reportedly identified in cypress oil (Callitirs glauca R. Br.), Callitirs intratropica, in the oil of Chamaecyparis obtusa and of Thujopsis dolabrata; the d,l-form is isolated from camphor oil. Also reported found in mandarin peel oil, swangi (Citrus hystrix D.C.), peppermint oil and black tea.

使用Citronellic acid was used in synthesis of stereoisomers of 3,11- dimethylnonacosan-2-one and 29-hydroxy-3,11-dimethylnonacosan-2-one.

調製方法

製造方法By oxidation of citronellal; also by the conversion of pulegone.

上流・下流製品情報

上流原料

β-シトロネロール N,N-ジメチルホルムアミドアセトントリオキソクロム(VI)ジエチルエーテル (無水)メタノールピリジン Propanedioic acid, 2-(1,5-dimethyl-4-hexen-1-yl)-, 1,3-diethyl ester 2-Pentanone, 5,5-dimethoxy-4-Methylpent-3-enylmagnesium bromide, 0.5M in THF (Z)-3,7-ジメチル-2,6-オクタジエン酸 (-)-β-シトロネロール

下流製品

7-イソプロピル-4-メチルオキセパン-2-オン

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シトロネル酸

基本情報

概要