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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.
| 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].
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| References | |
| 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. |
| Molecular Formula |
C16H26O7
|
|---|---|
| Molecular Weight |
330.3734
|
| Exact Mass |
330.168
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| Elemental Analysis |
C, 58.17; H, 7.93; O, 33.90
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| CAS # |
138-55-6
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| PubChem CID |
130796
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| Appearance |
White to off-white solid powder
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| Density |
1.31g/cm3
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| Boiling Point |
520.4ºC at 760mmHg
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| Melting Point |
196 ºC (ethyl acetate )
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| Flash Point |
187.1ºC
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| Vapour Pressure |
5.27E-13mmHg at 25°C
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| Index of Refraction |
1.561
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| LogP |
-0.5
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
4
|
| Heavy Atom Count |
23
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| Complexity |
473
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| 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
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| 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
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| 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
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| Synonyms |
Picrocrocin; Picrocrocine; Saffron-bitter;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~302.69 mM)
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|---|---|
| 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. View More
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. |
| 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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