Safranal

Safranal
IUPAC name

2,6,6-trimethyl-1,3-
cyclohexadiene-1-carboxaldehyde
Identifiers
CAS number 116-26-7 Y
PubChem 61041
ChemSpider 55000 Y
UNII 4393FR07EA Y
ChEBI CHEBI:53169 Y
Jmol-3D images Image 1
Properties
Molecular formula C10H14O
Molar mass 150.21 g/mol
Density 0.9734 g/cm3
Boiling point

70 °C at 1 mmHg
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Safranal is an organic compound isolated from saffron, the spice consisting of the stigmas of crocus flowers (Crocus sativus). It is the constituent primarily responsible for the aroma of saffron.

It is believed that safranal is a degradation product of the carotenoid zeaxanthin via the intermediacy of picrocrocin.

Pharmacology

Safranal is an effective anticonvulsant shown to act as an agonist at GABAA receptors.[1][2] Safranal also exhibits high antioxidant and free radical scavenging activity,[3][4] along with cytotoxicity towards cancer cells in vitro.[5] It has also been shown to have antidepressant properties.[6][7]

Natural sources

Natural sources of safranal include:[8]

References

  1. ^ Hosseinzadeh H, Talebzadeh F (December 2005). "Anticonvulsant evaluation of safranal and crocin from Crocus sativus in mice". Fitoterapia 76 (7–8): 722–4. doi:10.1016/j.fitote.2005.07.008. PMID 16253437. 
  2. ^ Hosseinzadeh H, Sadeghnia HR (April 2007). "Protective effect of safranal on pentylenetetrazol-induced seizures in the rat: involvement of GABAergic and opioids systems". Phytomedicine 14 (4): 256–62. doi:10.1016/j.phymed.2006.03.007. PMID 16707256. 
  3. ^ Hosseinzadeh H, Sadeghnia HR (2005). "Safranal, a constituent of Crocus sativus (saffron), attenuated cerebral ischemia induced oxidative damage in rat hippocampus". Journal of Pharmacy & Pharmaceutical Sciences 8 (3): 394–9. PMID 16401389. http://www.ualberta.ca/~csps/JPPS8(3)/H.Hosseinzadeh2/safranal.htm. 
  4. ^ Assimopoulou AN, Sinakos Z, Papageorgiou VP (November 2005). "Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents". Phytotherapy Research 19 (11): 997–1000. doi:10.1002/ptr.1749. PMID 16317646. 
  5. ^ Escribano J, Alonso GL, Coca-Prados M, Fernandez JA (February 1996). "Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro". Cancer Letters 100 (1–2): 23–30. doi:10.1016/0304-3835(95)04067-6. PMID 8620447. 
  6. ^ Hosseinzadeh H, Karimi G, Niapoor M (2004). "Antidepressant effect of Crocus sativus L. stigma extracts and their constituents, crocin and safranal, in mice". Acta Horticulturae 650: 435–45. http://www.actahort.org/books/650/650_54.htm. 
  7. ^ Akhondzadeh S, Fallah-Pour H, Afkham K, Jamshidi AH, Khalighi-Cigaroudi F (September 2004). "Comparison of Crocus sativus L. and imipramine in the treatment of mild to moderate depression: A pilot double-blind randomized trial ISRCTN45683816". BMC Complementary and Alternative Medicine 4: 12. doi:10.1186/1472-6882-4-12. PMC 517724. PMID 15341662. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=517724. 
  8. ^ "List of Chemicals". sun.ars-grin.gov. http://sun.ars-grin.gov:8080/npgspub/xsql/duke/listchempl2a.xsql?chem=Safranal&p_request=Go. Retrieved 2008-03-02. 
  9. ^ Yan JH, Tang KW, Zhong M, Deng NH (November 2002). "[Determination of chemical components of volatile oil from Cuminum cyminum L. by gas chromatography-mass spectrometry]" (in Chinese). Se Pu 20 (6): 569–72. PMID 12683011.