Picrocrocin

Picrocrocin
IUPAC name 4-(β-D-glucopyranosyloxy)- 2,6,6-trimethyl-1-cyclohexene- 1-carboxaldehyde
Identifiers
CAS number	138-55-6 Y
PubChem	130796
ChemSpider	115678 N
Jmol-3D images	Image 1
SMILES 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
InChI 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
Properties
Molecular formula	C16H26O7
Molar mass	330.37 g/mol
Melting point	154-156 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

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.^{[citation needed]}

References

(citation needed) Pfander, H.; Schurtenberger, H.; Biosynthesis of C20-carotenoids in Crocus sativus. Phytochemistry 1982, 21, 1039-1042. http://dx.doi.org/10.1016/S0031-9422(00)82412-7