Safranal

HCID 61041CAS 116-26-7
Substructure searchFind similar structures

Basic information

Standard SMILES
CC1=C(C=O)C(C)(C)CC=C1
InChIKey
SGAWOGXMMPSZPB-UHFFFAOYSA-N
Molecular formula
C10H14O
Average molar mass
150.22 g/mol
Monoisotopic mass
150.10446507

Overview

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.

Names & identifiers

Preferred name
Safranal
IUPAC
2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde
English name
SAFRANAL
Molecular formula
C10H14O
Molecular weight
150.22

Names & synonyms

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
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
11

Experimental & physicochemical properties

Fragrances · 2 items

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 items

Insoluble in water; soluble in oils

Miscible at room temperature (in ethanol)

Boiling Point · 2 items

70.00 °C. @ 1.00 mm Hg

70 °C (1 mm Hg);

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
70 °C1 · 70 °C1 mm Hg(lit.)
Density
0.966 g/mL · 0.966 g/mL at 25 °C(lit.)
vapor pressure
10.3 Pa · 10.3Pa at 20℃
FEMA
3389 · 3389 | 2,6,6-TRIMETHYLCYCLOHEXA-1,3-DIENYL METHANAL
refractive index
20 · n20/D 1.523(lit.)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 4 items

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%)

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07,GHS09

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Uses & manufacturing

IFRA Fragrance Standards · 6 items

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-β-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 items

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 Information1,3-Cyclohexadiene-1-carboxaldehyde, 2,6,6-trimethyl-: ACTIVE
Restriction Limits in the Finished Product (%) · 6 items

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)]

Applications · 2 items

OccurrenceOccurring 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.

UsesSafranal, 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.

Preparation methods

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

Upstream & downstream products

Suppliers50 total

苏州道澜生物医药科技有限公司15952404857 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
宁波君龙新材料有限公司0574 88552216 19032109277 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
合肥曼奇诺生物医药技术有限公司19719236623 · [email protected]

Additional notes

DefinitionChEBI: A monoterpenoid formally derived from beta-cyclocitral by dehydrogenation.

Related reactions

14 records
New reaction record

Linked notes

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