Picrocrocin Chemical Properties

Melting point:

196℃ (ethyl acetate )

alpha 

D20 -58° (c = 0.6)

Boiling point:

520.4±50.0 °C(Predicted)

Density 

1.31±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

4°C, protect from light

solubility 

Acetonitrile: Slightly Soluble
Methanol: Soluble
Water: Slightly Soluble

form 

Solid

pka

12.91±0.70(Predicted)

color 

White to off-white

InChI

InChI=1/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3/t9-,11-,12-,13+,14-,15-/s3

InChIKey

WMHJCSAICLADIN-LZYGGLMUNA-N

SMILES

[C@@H]1(O[C@H]2CC(C)(C)C(C=O)=C(C)C2)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O |&1:0,2,14,17,19,21,r|

LogP

-0.240 (est)

Picrocrocin Usage And Synthesis

Description

Picrocrocin, composing of safranal and glycoside, is one major compounds of saffron (Crocus sativus L. stigma), responsible for the bitter taste of saffron and a molecular marker of this spice, whose taste cannot be imitated from other spices or seasonings, and it can serve to identify true saffron. Saffron possesses various therapeutic activities such as antihypertensive, anticonvulsant, antitussive, antigenototoxic, anticancer, cytotoxic effects, anxiolytic, antioxidant, antidepressant, anti-inflammatory, and relaxant activity. As major bioactive compounds of saffron, picrocrocin also has some valuable medicinal properties similar as saffron, especially anticancer effect.

Antitumor activity

Picrocrocin as component of saffron displays same antitumor activity that have great potential for the prevention and treatment of various cancers through affecting cellular DNA and RNA synthesis and free radical scavenging activities of cancer. The experiments results for studying the effect of picrocrocin on proliferation of human tumoral cells (HeLa cell) in vitro showed that picrocrocin have a dose dependent inhibition of cell growth, and doses of picrocrocin inducing 50% inhibition of HeLa cell growth are 3 mM, in which picrocrocin have minor cytotoxicity for normal cells. Thus, picrocrocin can inhibit the growth of cancer cell. Other study results have showed that picrocrocin with highly bioaccessible could be transported quickly and reduced the proliferation of human adenocarcinoma and hepatocarcinoma cells.

Uses

Picrocrocin is a secondary metabolite of Saffron and has been found to be the taste component of saffron.

Definition

ChEBI: A beta-D-glucoside of beta-cyclocitral; the precursor of safranal. It is the compound most responsible for the bitter taste of saffron.

References

[1] MICHELE SPINELLI. Saffron Characterization by a Multidisciplinary Approach.[J]. Molecules, 2022, 28 1. DOI: 10.3390/molecules28010042
[2] GIANFRANCO DIRETTO. UGT709G1: a novel uridine diphosphate glycosyltransferase involved in the biosynthesis of picrocrocin, the precursor of safranal in saffron (Crocus sativus)[J]. New Phytologist, 2019, 224 2: 725-740. DOI: 10.1111/nph.16079
[3] JULIO ESCRIBANO . Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro[J]. Cancer letters, 1996, 100 1: Pages 23-30. DOI: 10.1016/0304-3835(95)04067-6

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