Picrocrocin

Picrocrocin
Names
	IUPAC name 4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde
Identifiers
CAS Number	138-55-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	115678 ;
PubChem CID	130796;
UNII	ON5B022511 ;
CompTox Dashboard (EPA)	DTXSID40160450 ;
	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 Key: WMHJCSAICLADIN-WYWSWGBSSA-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;
	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;
Properties
Chemical formula	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).

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.

References

^ 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.

Pfander, H.; Schurtenberger, H. (1982). "Biosynthesis of C20-carotenoids in Crocus sativus". Phytochemistry. 21 (5): 1039–1042. doi:10.1016/S0031-9422(00)82412-7.

[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.

[1]

Names

IUPAC name 4-(β-D-glucopyranosyloxy)-2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde
Identifiers
CAS Number	138-55-6
3D model (JSmol)	Interactive image
ChemSpider	115678
PubChem CID	130796
UNII	ON5B022511
CompTox Dashboard (EPA)	DTXSID40160450
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 Key: WMHJCSAICLADIN-WYWSWGBSSA-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
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
Properties
Chemical formula	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).