SAFRANAL

Names

[ CAS No. ]:
116-26-7

[ Name ]:
SAFRANAL

[Synonym ]:
MFCD00209531
2,6,6-trimethylcyclohexa-1,3-dienecarbaldehyde
2,3-Dihydro-2,2,6-trimethylbenzaldehyde
Safranal
2,6,6-Trimethylcyclohexa-1,3-dienyl methanal
2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde
1,3-CYCLOHEXADIENE-1-CARBOXALDEHYDE,2,6,6-TRIMETHYL
EINECS 204-133-7
FEMA No. 3389
2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde
1,1,3-Trimethyl-2-formylcyclohexa-2,4-diene

Biological Activity

[Description]:

Safranal is an orally active main component of Saffron (Crocus sativus) and is responsible for the unique aroma of this spice. Safranal has neuroprotective and anti-inflammatory effects and has the potential for Parkinson’s disease research[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[In Vitro]

Safranal (10-50 μM; for 1 h) dose-dependently decreases LPS-induced iNOS and COX-2 levels in both RAW264.7 cells and BMDMs[1]. Safranal (10-50 μM; for 1 h) inhibits cytokine IL-6 and TNF-α production and mRNA expression in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells[1]. Safranal (10, 50 μM; for 1 h followed by stimulation with 1 μg/ml of LPS for 30 min) inhibits the nuclear translocation of NF-κB and AP-1 in lipopolysaccharide (LPS)-stimulated RAW264.7 cells[1]. Western Blot Analysis[1] Cell Line: RAW264.7 cells and bone marrow-derived macrophages (BMDMs) Concentration: 10, 50 μM Incubation Time: For 1 h prior to lipopolysaccharide (LPS) stimulation (1 µg/ml) Result: Dose-dependently decreased LPS-induced iNOS and COX-2 levels in both RAW264.7 cells and BMDMs. Inhibited the phosphorylation of MAPK pathway proteins extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), p38. Inhibited NF-κB pathway proteins IKKα/β and IκBα and the degradation of IκBα. RT-PCR[1] Cell Line: RAW 264.7 cells Concentration: 10, 50 μM Incubation Time: For 1 h followed by stimulation with LPS (1 μg/ml) for 24 h Result: Inhibited cytokine IL-6 and TNF-α production and mRNA expression in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells.

[In Vivo]

Safranal (200-500 mg/kg; PO; for 7 days) causes a slight restoration of colon length and percentage of weight loss, and the DAI score is significantly low[1]. Animal Model: Female BALB/c mice (18-20 g) (DSS-induced colitis mice)[1] Dosage: 200, 500 mg/kg Administration: PO; for 7 days Result: Caused a slight restoration of colon length and percentage of weight loss, and the DAI score is significantly low.

[References]

[1]. Peeraphong Lertnimitphun, et al. Safranal Alleviates Dextran Sulfate Sodium-Induced Colitis and Suppresses Macrophage-Mediated Inflammation. Front Pharmacol. 2019 Nov 1;10:1281.

Chemical & Physical Properties

[ Density]:
0.975 g/cm3

[ Boiling Point ]:
217.3ºC at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₄O

[ Molecular Weight ]:
150.21800

[ Flash Point ]:
80.4ºC

[ Exact Mass ]:
150.10400

[ PSA ]:
17.07000

[ LogP ]:
2.48790

[ Vapour Pressure ]:
0.134mmHg at 25°C

[ Index of Refraction ]:
n20/D 1.523(lit.)

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ WGK Germany ]:
3

[ HS Code ]:
2912299000

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2912299000

[ Summary ]:
2912299000. other cyclic aldehydes without other oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

A fluorescence high throughput screening method for the detection of reactive electrophiles as potential skin sensitizers.

Toxicol. Appl. Pharmacol. 289 , 177-84, (2015)

Skin sensitization is an important toxicological end-point in the risk assessment of chemical allergens. Because of the complexity of the biological mechanisms associated with skin sensitization, inte...

Safranal of Crocus sativus L. inhibits inducible nitric oxide synthase and attenuates asthma in a mouse model of asthma.

Phytother Res. 29(4) , 617-27, (2015)

The present study involves evaluation of antioxidant potential of Crocus sativus and its main constituents, safranal (SFN) and crocin (CRO), in bronchial epithelial cells, followed antiinflammatory po...

Self-modeling curve resolution techniques applied to comparative analysis of volatile components of Iranian saffron from different regions.

Anal. Chim. Acta 662(2) , 143-54, (2010)

Volatile components of saffron from different regions of Iran were extracted by ultrasonic-assisted solvent extraction (USE) and were analyzed by gas chromatography-mass spectrometry (GC-MS). Self-mod...