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MedKoo Cat#: 330213 | Name: Picrocrocin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Picrocrocin is a monoterpene glycoside precursor of safranal. Picrocrocin is 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.

Chemical Structure

Picrocrocin
Picrocrocin
CAS#138-55-6

Theoretical Analysis

MedKoo Cat#: 330213

Name: Picrocrocin

CAS#: 138-55-6

Chemical Formula: C16H26O7

Exact Mass: 330.1679

Molecular Weight: 330.38

Elemental Analysis: C, 58.17; H, 7.93; O, 33.90

Price and Availability

Size Price Availability Quantity
100mg USD 2,650.00
200mg USD 3,250.00
500mg USD 4,250.00
1g USD 5,250.00
2g USD 8,450.00
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Related CAS #
No Data
Synonym
Picrocrocin; Picrocrocine; Saffron-bitter;
IUPAC/Chemical Name
(R)-2,6,6-trimethyl-4-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohex-1-ene-1-carbaldehyde
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
SMILES Code
O=CC1=C(C)C[C@@H](O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)CC1(C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
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.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Picrocrocin, an apocarotenoid found in Saffron. 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.
In vitro activity:
Picrocrocin exerted growth inhibitory effects on the SK-MEL-2 melanoma cells. The IC50 of picrocrocin against the SK-MEL-2 cells was 20 μM at 24-h incubation. The antiproliferative activity of picrocrocin was due to apoptosis and cell cycle arrest. In addition, picrocrocin enhanced the ROS levels and decreased the MMP levels of SK-MEL-2 cells. Finally, picrocrocin inhibited the JAK/STAT5 signalling pathway in the SK-MEL-2 melanoma cells. Reference: J BUON. 2018 Jul-Aug;23(4):1163-1168. https://pubmed.ncbi.nlm.nih.gov/30358226/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 83.0 251.23
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 330.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Yu L, Li J, Xiao M. 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. PMID: 30358226.
In vitro protocol:
Yu L, Li J, Xiao M. 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. PMID: 30358226.
In vivo protocol:
TBD
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Therapeutic effects of saffron (Crocus sativus L) on female reproductive system disorders: A systematic review. Phytother Res. 2024 Jun;38(6):2832-2846. doi: 10.1002/ptr.8186. Epub 2024 Apr 1. PMID: 38558480. 5: Bej E, Volpe AR, Cesare P, Cimini A, d'Angelo M, Castelli V. Therapeutic potential of saffron in brain disorders: From bench to bedside. Phytother Res. 2024 May;38(5):2482-2495. doi: 10.1002/ptr.8169. Epub 2024 Mar 6. PMID: 38446350. 6: Xiao L, Sun R, Han Y, Xia L, Lin K, Fu W, Zhong K, Ye Y. NAMPT‑NAD+ is involved in the senescence‑delaying effects of saffron in aging mice. Exp Ther Med. 2024 Feb 1;27(3):123. doi: 10.3892/etm.2024.12411. PMID: 38410190; PMCID: PMC10895469. 7: Etxebeste-Mitxeltorena M, Niza E, Fajardo CM, Gil C, Gómez-Gómez L, Martinez A, Ahrazem O. Neuroprotective properties of exosomes and chitosan nanoparticles of Tomafran, a bioengineered tomato enriched in crocins. Nat Prod Bioprospect. 2024 Jan 12;14(1):9. doi: 10.1007/s13659-023-00425-9. PMID: 38212507; PMCID: PMC10784249. 8: Ali A, Wani AB, Malla BA, Poyya J, Dar NJ, Ali F, Ahmad SB, Rehman MU, Nadeem A. Network Pharmacology Integrated Molecular Docking and Dynamics to Elucidate Saffron Compounds Targeting Human COX-2 Protein. Medicina (Kaunas). 2023 Nov 22;59(12):2058. doi: 10.3390/medicina59122058. PMID: 38138161; PMCID: PMC10744988. 9: Morote L, Rubio-Moraga Á, López Jiménez AJ, Aragonés V, Diretto G, Demurtas OC, Frusciante S, Ahrazem O, Daròs JA, Gómez-Gómez L. Verbascum species as a new source of saffron apocarotenoids and molecular tools for the biotechnological production of crocins and picrocrocin. Plant J. 2024 Apr;118(1):58-72. doi: 10.1111/tpj.16589. Epub 2023 Dec 15. PMID: 38100533. 10: Mena-García A, Sanz ML, Díez-Municio M, Ruiz-Matute AI. A Combined Gas and Liquid Chromatographic Approach for Quality Evaluation of Saffron-Based Food Supplements. Foods. 2023 Nov 9;12(22):4071. doi: 10.3390/foods12224071. PMID: 38002129; PMCID: PMC10670060. 11: Zohreh Vahedi S, Farhadian S, Shareghi B, Asgharzadeh S. Interaction between the antioxidant compound safranal and α-chymotrypsin in spectroscopic fields and molecular modeling approaches. J Biomol Struct Dyn. 2024 May;42(8):4097-4109. doi: 10.1080/07391102.2023.2272186. Epub 2023 Nov 15. PMID: 37969053. 12: Deng X, He S, Han Y, Chen Y. Metabolites profiling reveals the dynamic changes of non-volatiles in Pu-erh during Ganpu tea processing. Food Chem X. 2023 Jun 26;19:100774. doi: 10.1016/j.fochx.2023.100774. PMID: 37780327; PMCID: PMC10534103. 13: Aissa R, Ibourki M, Ait Bouzid H, Bijla L, Oubannin S, Sakar EH, Jadouali S, Hermansyah A, Goh KW, Ming LC, Bouyahya A, Gharby S. Phytochemistry, quality control and medicinal uses of Saffron (Crocus sativus L.): an updated review. J Med Life. 2023 Jun;16(6):822-836. doi: 10.25122/jml-2022-0353. PMID: 37675158; PMCID: PMC10478662. 14: Tiwari A, Modi SJ, Girme A, Hingorani L. Network pharmacology-based strategic prediction and target identification of apocarotenoids and carotenoids from standardized Kashmir saffron (Crocus sativus L.) extract against polycystic ovary syndrome. Medicine (Baltimore). 2023 Aug 11;102(32):e34514. doi: 10.1097/MD.0000000000034514. PMID: 37565925; PMCID: PMC10419424. 15: Avila-Sosa R, Nevárez-Moorillón GV, Ochoa-Velasco CE, Navarro-Cruz AR, Hernández-Carranza P, Cid-Pérez TS. Detection of Saffron's Main Bioactive Compounds and Their Relationship with Commercial Quality. Foods. 2022 Oct 18;11(20):3245. doi: 10.3390/foods11203245. PMID: 37430993; PMCID: PMC9601577. 16: Purohit A, Pawar L, Yadav SK. Structural and functional insights of a cold- adaptive β-glucosidase with very high glucose tolerance from Microbacterium sp. CIAB417. Enzyme Microb Technol. 2023 Sep;169:110284. doi: 10.1016/j.enzmictec.2023.110284. Epub 2023 Jun 30. PMID: 37406591. 17: Demurtas OC, Sulli M, Ferrante P, Mini P, Martí M, Aragonés V, Daròs JA, Giuliano G. Production of Saffron Apocarotenoids in Nicotiana benthamiana Plants Genome-Edited to Accumulate Zeaxanthin Precursor. Metabolites. 2023 Jun 6;13(6):729. doi: 10.3390/metabo13060729. PMID: 37367887; PMCID: PMC10305034. 18: Alighaleh P, Pakdel R, Ghanei Ghooshkhaneh N, Einafshar S, Rohani A, Saeidirad MH. Detection and Classification of Saffron Adulterants by Vis-Nir Imaging, Chemical Analysis, and Soft Computing. Foods. 2023 May 30;12(11):2192. doi: 10.3390/foods12112192. PMID: 37297436; PMCID: PMC10252310. 19: Drioiche A, Ailli A, Handaq N, Remok F, Elouardi M, Elouadni H, Al Kamaly O, Saleh A, Bouhrim M, Elazzouzi H, El Makhoukhi F, Zair T. Identification of Compounds of Crocus sativus by GC-MS and HPLC/UV-ESI-MS and Evaluation of Their Antioxidant, Antimicrobial, Anticoagulant, and Antidiabetic Properties. Pharmaceuticals (Basel). 2023 Apr 5;16(4):545. doi: 10.3390/ph16040545. PMID: 37111302; PMCID: PMC10144431. 20: Mena-García A, Herrero-Gutiérrez D, Sanz ML, Díez-Municio M, Ruiz-Matute AI. Fingerprint of Characteristic Saffron Compounds as Novel Standardization of Commercial Crocus sativus Extracts. Foods. 2023 Apr 13;12(8):1634. doi: 10.3390/foods12081634. PMID: 37107430; PMCID: PMC10137349.