Picrocrocin

Picrocrocin is a monoterpene glycoside precursor of safranal. It is found in the spice saffron, which comes from the crocus flower.[1] Picrocrocin has a bitter taste, and is the chemical most responsible for the taste of saffron.

Picrocrocin
Picrocrocin
Names
IUPAC name
(4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
Systematic IUPAC name
(4R)-2,6,6-Trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/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-/m1/s1 ☒N
    Key: WMHJCSAICLADIN-WYWSWGBSSA-N ☒N
  • 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-/m1/s1
    Key: WMHJCSAICLADIN-WYWSWGBSBU
  • O=C\C2=C(/C)C[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)CC2(C)C
Properties
C16H26O7
Molar mass 330.37 g/mol
Density 1.31 g/mL
Melting point 154 to 156 °C (309 to 313 °F; 427 to 429 K)
Boiling point 520.4 °C (968.7 °F; 793.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

During the drying process, picrocrocin liberates the aglycone (HTCC, C10H16O2) due to the action of the enzyme glucosidase. The aglycone is then transformed to safranal by dehydration. Picrocrocin is a degradation product of the carotenoid zeaxanthin.

Further information: Saffron § Chemistry

References
  1. Caballero-Ortega H, Pereda-Miranda R, Abdullaev FI (2007). "HPLC quantification of major active components from 11 different saffron (Crocus sativus L.) sources". Food Chemistry. 100 (3): 1126–1131. doi:10.1016/j.foodchem.2005.11.020.
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