Picrocrocin, a monoterpene glycoside precursor of safranal, is a natural product found in the spice saffron, which comes from the crocus flower. Picrocrocin is a degradation product of the carotenoid zeaxanthin. Picrocrocin exhibits growth inhibitory effects against SKMEL- 2 human malignant melanoma cells by targeting JAK/ STAT5 signaling pathway, cell cycle arrest and mitochondrial mediated apoptosis.

Physicochemical Properties

Molecular Formula	C16H26O7
Molecular Weight	330.3734
Exact Mass	330.168
Elemental Analysis	C, 58.17; H, 7.93; O, 33.90
CAS #	138-55-6
PubChem CID	130796
Appearance	White to off-white solid powder
Density	1.31g/cm3
Boiling Point	520.4ºC at 760mmHg
Melting Point	196 ºC (ethyl acetate )
Flash Point	187.1ºC
Vapour Pressure	5.27E-13mmHg at 25°C
Index of Refraction	1.561
LogP	-0.5
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Heavy Atom Count	23
Complexity	473
Defined Atom Stereocenter Count	6
SMILES	O([C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])[C@]1([H])C([H])([H])C(C([H])([H])[H])=C(C([H])=O)C(C([H])([H])[H])(C([H])([H])[H])C1([H])[H]
InChi Key	WMHJCSAICLADIN-WYWSWGBSSA-N
InChi Code	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
Chemical Name	(4R)-2,6,6-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexene-1-carbaldehyde
Synonyms	Picrocrocin; Picrocrocine; Saffron-bitter;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	SK-MEL-2 melanoma cells are inhibited in their ability to proliferate by picrocrocin. Following a 24-hour incubation period, the picrocrocin IC50 against SK-MEL-2 cells was 20 μM. Apoptosis and cell cycle arrest are the causes of picrocrocin's antiproliferative action. Furthermore, in SK-MEL-2 cells, picrocrocin can lower MMP levels and increase ROS levels. In conclusion, picrocrocin suppresses the SK-MEL-2 melanoma cells' JAK/STAT5 signaling pathway [1].
References	[1]. Picrocrocin exhibits growth inhibitory effects against SKMEL- 2 human malignant melanoma cells by targeting JAK/ STAT5 signaling pathway, cell cycle arrest and mitochondrial mediated apoptosis. J BUON. 2018 Jul-Aug;23(4):1163-1168.
Additional Infomation	Picrocrocin is a beta-D-glucoside of beta-cyclocitral; the precursor of safranal. It is the compound most responsible for the bitter taste of saffron. It is functionally related to a beta-cyclocitral. Picrocrocin has been reported in Crocus sativus, Crocus tommasinianus, and Crocus vernus with data available.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~302.69 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.0269 mL	15.1345 mL	30.2691 mL
	5 mM	0.6054 mL	3.0269 mL	6.0538 mL
	10 mM	0.3027 mL	1.5135 mL	3.0269 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.