Safranal

Safranal
Names
	IUPAC names 2,6,6-trimethyl-1,3-; cyclohexadiene-1-carboxaldehyde
Identifiers
CAS Number	116-26-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:53169 ;
ChemSpider	55000 ;
ECHA InfoCard	100.003.758
PubChem CID	61041;
UNII	4393FR07EA ;
CompTox Dashboard (EPA)	DTXSID7049398 ;
	InChI InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 Key: SGAWOGXMMPSZPB-UHFFFAOYSA-N ; InChI=1/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 Key: SGAWOGXMMPSZPB-UHFFFAOYAY;
	SMILES O=C\C1=C(\C=C/CC1(C)C)C;
Properties
Chemical formula	C10H14O
Molar mass	150.21 g/mol
Density	0.9734 g/cm3
Boiling point	70 °C at 1 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 GABA_A 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]

Aspalathus linearis (Rooibos)
Camellia sinensis (Tea leaf)
Crocus sativus (Saffron)
Ficus carica (Fig leaf)
Lycium chinense (Wolfberry)
Cuminum cyminum (Cumin Seed)^[9]

References

^ Hosseinzadeh H, Talebzadeh F (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. {{cite journal}}: Unknown parameter |month= ignored (help)
^ Hosseinzadeh H, Sadeghnia HR (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. {{cite journal}}: Unknown parameter |month= ignored (help)
^ 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.
^ Assimopoulou AN, Sinakos Z, Papageorgiou VP (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Escribano J, Alonso GL, Coca-Prados M, Fernandez JA (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Akhondzadeh S, Fallah-Pour H, Afkham K, Jamshidi AH, Khalighi-Cigaroudi F (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
^ "List of Chemicals". sun.ars-grin.gov. Retrieved 2008-03-02.^{[unreliable source?]}
^ Yan JH, Tang KW, Zhong M, Deng NH (2002). "[Determination of chemical components of volatile oil from Cuminum cyminum L. by gas chromatography-mass spectrometry]". Se Pu (in Chinese). 20 (6): 569–72. PMID 12683011. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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[anticonvulsant-Hosseinzadeh-1] Hosseinzadeh H, Talebzadeh F (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. {{cite journal}}: Unknown parameter |month= ignored (help)

[protective-effect-Hosseinzadeh-2] Hosseinzadeh H, Sadeghnia HR (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. {{cite journal}}: Unknown parameter |month= ignored (help)

[Safranal-a-constituent-Hosseinzadeh-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.

[Radical-scavenging-Assimopoulou-4] Assimopoulou AN, Sinakos Z, Papageorgiou VP (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[Crocin-safranal-Escribano-5] Escribano J, Alonso GL, Coca-Prados M, Fernandez JA (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[7] Akhondzadeh S, Fallah-Pour H, Afkham K, Jamshidi AH, Khalighi-Cigaroudi F (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)

[8] "List of Chemicals". sun.ars-grin.gov. Retrieved 2008-03-02.^{[unreliable source?]}

[9] Yan JH, Tang KW, Zhong M, Deng NH (2002). "[Determination of chemical components of volatile oil from Cuminum cyminum L. by gas chromatography-mass spectrometry]". Se Pu (in Chinese). 20 (6): 569–72. PMID 12683011. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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