Crocine

Crocine
Structuurformule en molecuulmodel
	crocine
Algemeen
Chemische formule	C44H64O24
IUPAC-naam	bis[(2S,3R,4S,5S,6R)- 3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R) -3,4,5-trihydroxy-6-(hydroxymethyl)oxan- 2-yl]oxymethyl]oxan-2-yl](2E,4E,6E, 8E,10E,12E,14E)-2,6,11,15- tetramethylhexadeca-2,4,6,8,10, 12,14-heptaeendioaat
Andere namen	crocine; alfa-crocine
Molaire massa	976,96 g/mol
SMILES	Zie voetnoot
CAS-nummer	42553-65-1
EG-nummer	255-881-6
PubChem	5281233
Wikidata	Q424767
Beschrijving	rode kristallen
Fysische eigenschappen
Aggregatietoestand	vast
Kleur	rood
Smeltpunt	186 °C
Goed oplosbaar in	water
Tenzij anders vermeld zijn standaardomstandigheden gebruikt (298,15 K of 25 °C, 1 bar).
Portaal	Scheikunde

Crocine is een chemische verbinding uit de carotenoïden, die voorkomt in de bloemen van de saffraankrokus (Crocus sativus, waar de stof haar naam aan ontleent) en de Kaapse jasmijn (Gardenia jasminoides).

Crocine is een di-ester gevormd door het dicarbonzuur crocetine en twee moleculen gentiobiose.

Crocine vormt in zuivere toestand intens rode kristallen. Het is goed oplosbaar in water; de oplossing heeft een oranje kleur. De kleur van saffraan is hoofdzakelijk afkomstig van de crocine.

Onderzoek heeft uitgewezen dat de stof antioxidante eigenschappen heeft.

Crocine, evenals safranal en picrocrocine die ook in saffraan voorkomen, bleek bij in-vitroproeven ook in staat om de groei van kankercellen te remmen.

Crocine en safranal vertonen ook antidepressieve eigenschappen.

Bronnen, noten en/of referenties

↑ SMILES (symbolische structuurweergave) =
CC(=CC=CC=C(C)C=CC=C(C)C(=O)OC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)C=CC=C(C)C(=O)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O
↑ Crocin Chemical Information
↑ MA. Papandreou, CD. Kanakis, MG. Polissiou, S. Efthimiopoulos, P. Cordopatis, M. Margarity, FN. Lamari (2006) "Inhibitory activity on amyloid-beta aggregation and antioxidant properties of Crocus sativus stigmas extract and its crocin constituents.". J Agric Food Chem. 54 (23): 8762–8. PMID 17090119.
↑ T. Ochiai et al. (2006) "Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo.". Biochim Biophys Acta. 1770 (4): 578-584. PMID 17215084.
↑ YQ. Zheng, JX. Liu, JN. Wang, L. Xu (2006) "Effects of crocin on reperfusion-induced oxidative/nitrative injury to cerebral microvessels after global cerebral ischemia.". Brain Res. 1138: 86-94. PMID 17274961.
↑ J. Escribano, GL. Alonso, M. Coca-Prados, JA. Fernandez (1996) "Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro.". Cancer Letters 100 (1-2): 22-30. PMID 8620447.
↑ DG. Chryssanthi, FN. Lamari, G. Iatrou, A. Pylara, NK. Karamanos, P. Cordopatis (2007) "Inhibition of breast cancer cell proliferation by style constituents of different Crocus species.". Anticancer Research 27 (1A): 357-62. PMID 17352254.
↑ F. Abdullaev Jafarova, H. Caballero-Ortega, L. Riverón-Negrete, R. Pereda-Miranda, R. Rivera-Luna, J. Manuel Hernández, I. Pérez-López, JJ. Espinosa-Aguirre (2002) "In vitro evaluation of the chemopreventive potential of saffron.". Rev. Invest. Clin. 54 (5): 430-6. PMID 12587418.
↑ (en) Renata Matraszek-Gawron, Mirosława Chwil, Karol Terlecki, Michał Marian Skoczylas, Current Knowledge of the Antidepressant Activity of Chemical Compounds from Crocus sativus L.. National Library of Medicine (16 januari 2023). Geraadpleegd op 10 augustus 2023.
↑ Akhondzadeh, Shahin, Fallah-Pour, Hasan, Afkham, Khosro, Jamshidi, Amir-Hossein, Khalighi-Cigaroudi, Farahnaz (2 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. ISSN:1472-6882. PMID: 15341662. DOI:10.1186/1472-6882-4-12.

[1] SMILES (symbolische structuurweergave) =
CC(=CC=CC=C(C)C=CC=C(C)C(=O)OC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)C=CC=C(C)C(=O)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O

[2] Crocin Chemical Information

[3] MA. Papandreou, CD. Kanakis, MG. Polissiou, S. Efthimiopoulos, P. Cordopatis, M. Margarity, FN. Lamari (2006) "Inhibitory activity on amyloid-beta aggregation and antioxidant properties of Crocus sativus stigmas extract and its crocin constituents.". J Agric Food Chem. 54 (23): 8762–8. PMID 17090119.

[4] T. Ochiai et al. (2006) "Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo.". Biochim Biophys Acta. 1770 (4): 578-584. PMID 17215084.

[5] YQ. Zheng, JX. Liu, JN. Wang, L. Xu (2006) "Effects of crocin on reperfusion-induced oxidative/nitrative injury to cerebral microvessels after global cerebral ischemia.". Brain Res. 1138: 86-94. PMID 17274961.

[6] J. Escribano, GL. Alonso, M. Coca-Prados, JA. Fernandez (1996) "Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro.". Cancer Letters 100 (1-2): 22-30. PMID 8620447.

[7] DG. Chryssanthi, FN. Lamari, G. Iatrou, A. Pylara, NK. Karamanos, P. Cordopatis (2007) "Inhibition of breast cancer cell proliferation by style constituents of different Crocus species.". Anticancer Research 27 (1A): 357-62. PMID 17352254.

[8] F. Abdullaev Jafarova, H. Caballero-Ortega, L. Riverón-Negrete, R. Pereda-Miranda, R. Rivera-Luna, J. Manuel Hernández, I. Pérez-López, JJ. Espinosa-Aguirre (2002) "In vitro evaluation of the chemopreventive potential of saffron.". Rev. Invest. Clin. 54 (5): 430-6. PMID 12587418.

[9] (en) Renata Matraszek-Gawron, Mirosława Chwil, Karol Terlecki, Michał Marian Skoczylas, Current Knowledge of the Antidepressant Activity of Chemical Compounds from Crocus sativus L.. National Library of Medicine (16 januari 2023). Geraadpleegd op 10 augustus 2023.

[10] Akhondzadeh, Shahin, Fallah-Pour, Hasan, Afkham, Khosro, Jamshidi, Amir-Hossein, Khalighi-Cigaroudi, Farahnaz (2 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. ISSN:1472-6882. PMID: 15341662. DOI:10.1186/1472-6882-4-12.