Safranal

Last updated
Safranal
Safranal.svg
Names
Preferred IUPAC name
2,6,6-Trimethylcyclohexa-1,3-diene-1-carbaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.758 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 Yes check.svgY
    Key: SGAWOGXMMPSZPB-UHFFFAOYSA-N Yes check.svgY
  • O=C\C1=C(\C=C/CC1(C)C)C
Properties
C10H14O
Molar mass 150.21 g/mol
Density 0.9734 g/cm3
Boiling point 70 °C (158 °F; 343 K) at 1 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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

Pharmacology

Safranal is an effective anticonvulsant in animal models, 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] One of its anticancer mechanisms of action involves disruption of the normal assembly dynamics of cellular microtubules. [6] It has also been shown to have antidepressant properties in animals and pilot studies in humans. [7] [8]

Natural sources

Natural sources of safranal include: [9] [ unreliable source? ]

Related Research Articles

<span class="mw-page-title-main">Saffron</span> Spice made from crocus flowers

Saffron is a spice derived from the flower of Crocus sativus, commonly known as the "saffron crocus". The vivid crimson stigma and styles, called threads, are collected and dried for use mainly as a seasoning and colouring agent in food. Although some doubts remain on its origin, it is believed that saffron originated in Iran. However, Greece and Mesopotamia have also been suggested as the possible region of origin of this plant. Saffron crocus slowly propagated throughout much of Eurasia and was later brought to parts of North Africa, North America, and Oceania.

<i>Crocus</i> Genus of flowering plants in the family Iridaceae

Crocus is a genus of seasonal flowering plants in the family Iridaceae comprising about 100 species of perennials growing from corms. They are low growing plants, whose flower stems remain underground, that bear relatively large white, yellow, orange or purple flowers and then become dormant after flowering. Many are cultivated for their flowers, appearing in autumn, winter, or spring. The flowers close at night and in overcast weather conditions. The crocus has been known throughout recorded history, mainly as the source of saffron. Saffron is obtained from the dried stigma of Crocus sativus, an autumn-blooming species. It is valued as a spice and dyestuff, and is one of the most expensive spices in the world. Iran is the center of saffron production. Crocuses are native to woodland, scrub, and meadows from sea level to alpine tundra from the Mediterranean, through North Africa, central and southern Europe, the islands of the Aegean, the Middle East and across Central Asia to Xinjiang in western China. Crocuses may be propagated from seed or from daughter cormels formed on the corm, that eventually produce mature plants. They arrived in Europe from Turkey in the 16th century and became valued as an ornamental flowering plant.

<span class="mw-page-title-main">Naringenin</span> Chemical compound

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs.

<i>Crocus sativus</i> Species of plant, saffron crocus

Crocus sativus, commonly known as saffron crocus or autumn crocus, is a species of flowering plant in the iris family Iridaceae. A cormous autumn-flowering cultivated perennial, unknown in the wild, it is best known for the culinary use of its floral stigmas as the spice saffron. Human cultivation of saffron crocus and the trade and use of saffron have endured for more than 3,500 years and span different cultures, continents, and civilizations.

<span class="mw-page-title-main">Picrocrocin</span> Chemical compound

Picrocrocin is a monoterpene glycoside precursor of safranal. It is found in the spice saffron, which comes from the crocus flower. Picrocrocin has a bitter taste, and is the chemical most responsible for the taste of saffron.

<i>Crocus cartwrightianus</i> Species of flowering plant

Crocus cartwrightianus is a species of flowering plant in the family Iridaceae, native to mainland Greece and Crete. It is a cormous perennial growing to 5 cm (2 in). The flowers, in shades of lilac or white with purple veins and prominent red stigmas, appear with the leaves in autumn and winter.

<span class="mw-page-title-main">History of saffron</span> History cultivation and use of the spice

Human cultivation and use of saffron spans more than 3,500 years and extends across cultures, continents, and civilizations. Saffron, a spice derived from the dried stigmas of the saffron crocus, has through history remained among the world's most costly substances. With its bitter taste, hay-like fragrance, and slight metallic notes, the apocarotenoid-rich saffron has been used as a seasoning, fragrance, dye, and medicine.

<span class="mw-page-title-main">Crocin</span> Carotenoid chemical compound

Crocin is a carotenoid chemical compound that is found in the flowers of crocus and gardenia. Its oxygen content also chemically makes it a xanthene. Crocin is the chemical primarily responsible for the color of saffron.

<span class="mw-page-title-main">Crocetin</span> Carotenoid Chemical compound

Crocetin is a natural apocarotenoid dicarboxylic acid that is found in the crocus flower together with its glycoside, crocin, and Gardenia jasminoides fruits. It is also known as crocetic acid. It forms brick red crystals with a melting point of 285°C.

β-Pinene Chemical compound

β-Pinene is a monoterpene, an organic compound found in plants. It is one of the two isomers of pinene, the other being α-pinene. It is colorless liquid soluble in alcohol, but not water. It has a woody-green pine-like smell.

<span class="mw-page-title-main">Siramesine</span> Chemical compound

Siramesine is a sigma receptor agonist, selective for the σ2 subtype. In animal studies, siramesine has been shown to produce anxiolytic and antidepressant effects. It was developed by the pharmaceutical company H Lundbeck for the treatment of anxiety, although development was discontinued after clinical trials showed a lack of efficacy in humans. Siramesine has been shown to produce an enhanced antidepressant effect when co-administered with NMDA antagonists. It has also been used to study the σ2 activity of cocaine, and has been shown to produce anticancer properties both in vitro and in vivo.

<span class="mw-page-title-main">KIAA1524</span> Protein-coding gene in the species Homo sapiens

Protein CIP2A also known as cancerous inhibitor of PP2A (CIP2A) is a protein that in humans is encoded by the KIAA1524 gene.

<span class="mw-page-title-main">Demecolcine</span> Chemical compound

Demecolcine is a drug used in chemotherapy. It is closely related to the natural alkaloid colchicine with the replacement of the acetyl group on the amino moiety with methyl, but it is less toxic. It depolymerises microtubules and limits microtubule formation, thus arresting cells in metaphase and allowing cell harvest and karyotyping to be performed.

In pharmacology, a GABA transaminase inhibitor is an enzyme inhibitor that acts upon GABA transaminase. Inhibition of GABA transaminase enzymes reduces the degradation of GABA, leading to increased neuronal GABA concentrations.

<span class="mw-page-title-main">Wogonin</span> Chemical compound

Wogonin is an O-methylated flavone, a flavonoid-like chemical compound which is found in Scutellaria baicalensis.

<span class="mw-page-title-main">Amentoflavone</span> Chemical compound

Amentoflavone is a biflavonoid constituent of a number of plants including Ginkgo biloba, Chamaecyparis obtusa (hinoki), Biophytum sensitivum, Selaginella tamariscina, Hypericum perforatum and Xerophyta plicata.

<span class="mw-page-title-main">Pyr1</span> Chemical compound

Pyr1 (LIMINIB) is an organic compound composed of carbon, hydrogen, oxygen and nitrogen that inhibits the enzyme LIM kinase.

Crocetin glucosyltransferase is an enzyme with systematic name UDP-glucose:crocetin 8-O-D-glucosyltransferase. This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Cumin</span> Species of plant with seeds used as a spice

Cumin is a flowering plant in the family Apiaceae, native to the Irano-Turanian Region. Its seeds – each one contained within a fruit, which is dried – are used in the cuisines of many cultures in both whole and ground form. Although cumin is used in traditional medicine, there is no high-quality evidence that it is safe or effective as a therapeutic agent.

Saffron is one of the world's most expensive spices by weight due to its difficulty to harvest. Saffron consists of stigmas plucked from the vegetatively propagated and sterile Crocus sativus, known popularly as the saffron crocus. The resulting dried "threads" are distinguished by their bitter taste, hay-like fragrance, and slight metallic notes. The saffron crocus is unknown in the wild; its most likely precursor, Crocus cartwrightianus, originated in Crete or Central Asia; The saffron crocus is native to Southwest Asia, and is believed to have been first cultivated in Iran. Greece, Turkey, and Kashmir (India) have also been suggested as possible sites of origin.

"Saffron, for example, was once less regarded than it is today because the crocus from which it is extracted was not particularly mysterious. It flourished in European locations extending from Asia Minor, where it originated, to Saffron Walden in England, where it was naturalised. Only subsequently, when its labour-intensive cultivation became largely centred in Kashmir (India), did it seem sufficiently exotic to qualify as one of the most precious of spices."

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.
  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. S2CID   23907085.
  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. Cheriyamundath S, Choudhary S, and Lopus M (2017) Safranal inhibits HeLa cell viability by perturbing the reassembly potential of microtubules. Phytother Res, 32, 170-173. doi: 10.1002/ptr.5938. PMID   29024138
  7. 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 (650): 435–45. doi:10.17660/ActaHortic.2004.650.54.
  8. 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.
  9. "List of Chemicals". sun.ars-grin.gov. Retrieved 2008-03-02.
  10. 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]". Se Pu (in Chinese). 20 (6): 569–72. PMID   12683011.
  11. 1 2 3 4 5 6 7 8 Ramin Rezaee; Hossein Hosseinzadeh (January 2013). "[Safranal: From an Aromatic Natural Product to a Rewarding Pharmacological Agent]". Iranian Journal of Basic Medical Sciences. 16 (1): 12–26. PMC   3637901 . PMID   23638289.