Safranal (HCID 61041)

概要

Safranal is a monoterpenoid formally derived from beta-cyclocitral by dehydrogenation. It is the major volatile component of saffron responsible for the characteristic aroma of saffron. It has a role as an antineoplastic agent, a radical scavenger, a neuroprotective agent, an anti-inflammatory agent, a nephroprotective agent and a plant metabolite. It is functionally related to a beta-cyclocitral.

名称と識別子

優先名称: Safranal
IUPAC: 2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde
現地名: 2,6,6-トリメチル-1,3-シクロヘキサジエン-1-カルボアルデヒド
英語名: SAFRANAL
分子式: C10H14O
分子量: 150.22

名称と別名

Safranal116-26-72,3-Dihydro-2,2,6-trimethylbenzaldehyde2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde1,3-CYCLOHEXADIENE-1-CARBOXALDEHYDE, 2,6,6-TRIMETHYL-2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehydeDehydro-beta-cyclocitral2,6,6-Trimethyl-1,3-cyclohexadienal(2,6,6-Trimethylcyclohexa-1,3-dienyl)methanalFEMA No. 3389DTXSID70493981,1,3-Trimethyl-2-formylcyclohexa-2,4-diene

名称をさらに表示

2,6,6-トリメチル-1,3-シクロヘキサジエン-1-カルバルデヒドサフラナール2,6,6-トリメチル-1,3-シクロヘキサジエン-1-カルボアルデヒドサフラナール (>80%)FEMA 33892,3-Dihydro-2,2,6-trimethylbenzalhydeSAFRANAL 88+%Safranal (>80%)

2,6,6-Trimethylcyclohexa-1,3-dienyl methanalCHEBI:531694393FR07EADTXCID4029357RefChem:884355204-133-72,6,6-trimethylcyclohexa-1,3-dienecarbaldehydeMFCD00209531

データベース識別子

CAS: 116-26-7
PubChem CID: 61041
DTXSID: DTXSID7049398
ChEMBL: CHEMBL3183495
ChEBI: CHEBI:53169
UNII: 4393FR07EA
EC Number: 204-133-7
Nikkaji: J5.278G

物性

構造計算による物性

XLogP: 2.1
極性表面積: 17.1 Å²
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: 1
重原子数: 11
形式電荷: 0
複雑度: 231

実験および物理化学的性質

Fragrances · 2 件

Fragrance substance (2,6,6-Trimethylcyclohex-1,3-dienyl methanal) -> IFRA amendment 49

Fragrance Ingredient (2,6,6-Trimethylcyclohexa-1,3-dienyl methanal) -> IFRA transparency List

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

Density0.968-0.980 (20 °C)

Flavoring AgentsEU Flavoring substances

Solubility · 2 件

Insoluble in water; soluble in oils

Miscible at room temperature (in ethanol)

Boiling Point · 2 件

70.00 °C. @ 1.00 mm Hg

70 °C (1 mm Hg);

物理化学的性質

融点: 25 °C · <25 °C
沸点: 70 °C1 · 70 °C1 mm Hg(lit.)
比重(密度): 0.966 g/mL · 0.966 g/mL at 25 °C(lit.)
蒸気圧: 10.3 Pa · 10.3Pa at 20℃
FEMA: 3389 · 3389 | 2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIENYL METHANAL
屈折率: 20 · n20/D 1.523(lit.)
闪点: 186 °F · 186 °F
貯蔵温度: -20 °C · Inert atmosphere,Store in freezer, under -20°C
溶解性: クロロホルム、酢酸エチル（微量）、メタノール（微量）
外見: 油
色: イエローからダークイエロー
臭い (Odor): 1 %。フレッシュハーブ、フェノール、メタリック、ローズマリー、タバコ、スパイシー · ジプロピレングリコール中1.00%。フレッシュハーブ、フェノール、メタリック、ローズマリー、タバコ、スパイシー
においのタイプ: ハーブ
由来生物: synthetic
水溶解度: 514.9 mg/L · 514.9mg/L at 20℃
Merck: 13 · 13,8394
JECFA Number: 977 · 977
BRN: 1932918 · 1932918
安定性: 光に敏感
主な用途: フレーバーそして香料
化粧品成分の機能: 香料
InChI: 1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3
InChIKey: SGAWOGXMMPSZPB-UHFFFAOYSA-N
SMILES: CC1=C(C=O)C(C)(C)CC=C1
LogP: 2.7 at · 2.7 at 20℃
EPAの化学物質情報: 1 · 1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl- (116-26-7)

化学的性質

化学的特性2,6,6-Trimethylcyclohexa-1,3-dienyl methanal has a characteristic saffron-like odor and taste.

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (80.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P273, 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 1700 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: 1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl-

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

Status: Active Update: 01-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/17302

1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl-: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 4 (80.4%)

安全データ

wgk: 3
tsca: TSCA listed
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
Hazard Classifications: Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1A
ストレージクラス: 10 - Combustible liquids

化学と産業

薬理情報

Cellular LocationsExtracellular

用途と製造

IFRA Fragrance Standards · 6 件

2,6,6-Trimethylcyclohex-1,3-dienyl methanal

2,6,6-Trimethylcyclohexa-1,3-diene-1-carbaldehyde; 2,6,6-Trimethyl-1,3-cyclohexadienal; 2,6,6-Trimethyl-1,3-cyclohexadien-1-carboxaldehyde; 1,1,3-Trimethyl-2-formylcyclohexa-2,4-diene; Dehydro-Î²-cyclocitral; Safranal (commercial name)

IFRA_STD_082.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

General Manufacturing Information1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl-: ACTIVE

Restriction Limits in the Finished Product (%) · 6 件

0.0022 [Products applied to the lips]

0.00066 [Products applied to the axillae]

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

0.012 [Products related to fine fragrances]

0.0032 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]

0.0032 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]

応用分野 · 3 件

解説サフラナール．単環性モノテルペンアルデヒド．ヒガンバナ科サフランCrocus sativusの花に含まれている苦味配糖体ビクロクロシンC16H26O7を加水分解するとブドウ糖とサフラナールが生成する．沸点70 ℃(133 Pa)．[α]D190.9734．nD191.5281．

天然物の起源Occurring naturally as a glucoside (picrocrocin) in saffron. Also reported found in grapefruit juice, saffron, black tea, green tea, microbial fermented tea, Bourbon vanilla, lemon balm, grapefruit juice, maté and sweet grass oil.

使用Safranal, is isolated from Saffron, and is primarily responsible for the aroma of saffron. It has also been shown to have anticonvulsant properties, acting as agonist at GABAA receptors. It is also possessing anticancer and antidepressant properties.

調製方法

製造方法By acid hydrolysis of picrocrocin, the bitter principle in saffron; by catalytic dehydrogenation of β-cyclocitral or α-cyclogeranic acid with selenium dioxide.