Safranal (HCID 61041)

개요

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.

이름 및 식별자

우선 이름: Safranal
IUPAC: 2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde
영어명: SAFRANAL
분자식: C10H14O
분자량: 150.22

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 2.1
극성 표면적: 17.1 Å²
수소 결합 공여자 수: 0
수소 결합 수용자 수: 1
회전 가능 결합 수: 1
무거운 원자 수: 11
형식 전하: 0
복잡도: 231

실험 및 물리화학적 성질

Fragrances · 2건

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 · 2건

Insoluble in water; soluble in oils

Miscible at room temperature (in ethanol)

Boiling Point · 2건

70.00 °C. @ 1.00 mm Hg

70 °C (1 mm Hg);

물리화학적 성질

녹는점: 25 °C · <25 °C
끓는 점: 70 °C1 · 70 °C1 mm Hg(lit.)
밀도: 0.966 g/mL · 0.966 g/mL at 25 °C(lit.)
증기압: 10.3 Pa · 10.3Pa at 20℃
FEMA: 3389 · 3389 | 2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIENYL METHANAL
굴절률: 20 · n20/D 1.523(lit.)
인화점: 186 °F · 186 °F
저장 조건: -20 °C · Inert atmosphere,Store in freezer, under -20°C
용해도: 클로로포름, 아세트산에틸(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태: 기름
색상: 노란색에서 진한 노란색까지
냄새: 1 % · 디프로필렌 글리콜 중 1.00%. 신선한 허브 페놀릭 메탈릭 로즈마리 담배 매운맛
냄새 유형: 약초
생물학적 소스: synthetic
수용성: 514.9 mg/L · 514.9mg/L at 20℃
Merck: 13 · 13,8394
JECFA Number: 977 · 977
BRN: 1932918 · 1932918
안정성: 감광성
주요 응용: 향료 및 향
화장품 원료 기능: 향수
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: 1 · 1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl- (116-26-7)

화학적 성질

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

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Regulatory Information · 4건

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%)

안전 데이터

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
스토리지 클래스: 10 - Combustible liquids

화학 및 산업

약리 정보

Cellular LocationsExtracellular

용도 및 제조

IFRA Fragrance Standards · 6건

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 · 6건

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 (%) · 6건

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)]

응용 분야 · 2건

출처Occurring 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.

용도Safranal, 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.

제조 방법

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