Picrocrocin
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MedKoo CAT#: 330213

CAS#: 138-55-6

Description: 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.


Price and Availability

Size
Price

100mg
USD 2650
1g
USD 5250
Size
Price

200mg
USD 3250
2g
USD 8450
Size
Price

500mg
USD 4250

Picrocrocin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 330213
Name: Picrocrocin
CAS#: 138-55-6
Chemical Formula: C16H26O7
Exact Mass: 330.1679
Molecular Weight: 330.377
Elemental Analysis: C, 58.17; H, 7.93; O, 33.90


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


Technical Data

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).

Harmonized System Code:
2934.99.90.01


Additional Information

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.


References

1: Moratalla-López N, Bagur MJ, Lorenzo C, Salinas MEMR, Alonso GL. Bioactivity and Bioavailability of the Major Metabolites of Crocus sativus L. Flower. Molecules. 2019 Aug 2;24(15). pii: E2827. doi: 10.3390/molecules24152827. Review. PubMed PMID: 31382514; PubMed Central PMCID: PMC6696252.

2: Diretto G, Ahrazem O, Rubio-Moraga Á, Fiore A, Sevi F, Argandoña J, Gómez-Gómez L. UGT709G1: a novel uridine diphosphate glycosyltransferase involved in the biosynthesis of picrocrocin, the precursor of safranal in saffron (Crocus sativus). New Phytol. 2019 Oct;224(2):725-740. doi: 10.1111/nph.16079. Epub 2019 Aug 29. PubMed PMID: 31356694.

3: Cardone L, Castronuovo D, Perniola M, Cicco N, Candido V. Evaluation of corm origin and climatic conditions on saffron (Crocus sativus L.) yield and quality. J Sci Food Agric. 2019 Oct;99(13):5858-5869. doi: 10.1002/jsfa.9860. Epub 2019 Jul 10. PubMed PMID: 31206680.

4: Parizad S, Dizadji A, Habibi MK, Winter S, Kalantari S, Movi S, Lorenzo Tendero C, Alonso GL, Moratalla-Lopez N. The effects of geographical origin and virus infection on the saffron (Crocus sativus L.) quality. Food Chem. 2019 Oct 15;295:387-394. doi: 10.1016/j.foodchem.2019.05.116. Epub 2019 May 17. PubMed PMID: 31174773.

5: Babaei S, Niknam V, Behmanesh M. Nitric oxide induced carotenoid contents in Crocus sativus under salinity. Nat Prod Res. 2019 May 14:1-5. doi: 10.1080/14786419.2019.1608544. [Epub ahead of print] PubMed PMID: 31084371.

6: Tan H, Chen X, Liang N, Chen R, Chen J, Hu C, Li Q, Li Q, Pei W, Xiao W, Yuan Y, Chen W, Zhang L. Transcriptome analysis reveals novel enzymes for apo-carotenoid biosynthesis in saffron and allows construction of a pathway for crocetin synthesis in yeast. J Exp Bot. 2019 Sep 24;70(18):4819-4834. doi: 10.1093/jxb/erz211. PubMed PMID: 31056664.

7: Aghaei Z, Jafari SM, Dehnad D. Effect of Different Drying Methods on the Physicochemical Properties and Bioactive Components of Saffron Powder. Plant Foods Hum Nutr. 2019 Jun;74(2):171-178. doi: 10.1007/s11130-019-00729-7. PubMed PMID: 31001725.

8: Mykhailenko O, Kovalyov V, Goryacha O, Ivanauskas L, Georgiyants V. Biologically active compounds and pharmacological activities of species of the genus Crocus: A review. Phytochemistry. 2019 Jun;162:56-89. doi: 10.1016/j.phytochem.2019.02.004. Epub 2019 Mar 8. Review. PubMed PMID: 30856530.

9: Yuan Y, Deng Y, Wang J, Chen R. A rapid site-specific PCR based one-tube authentication method for saffron in crude drugs and processed herbal medicines. Electrophoresis. 2018 Dec 21. doi: 10.1002/elps.201800467. [Epub ahead of print] PubMed PMID: 30575987.

10: Siddiqui MJ, Saleh MSM, Basharuddin SNBB, Zamri SHB, Mohd Najib MHB, Che Ibrahim MZB, Binti Mohd Noor NA, Binti Mazha HN, Mohd Hassan N, Khatib A. Saffron (Crocus sativus L.): As an Antidepressant. J Pharm Bioallied Sci. 2018 Oct-Dec;10(4):173-180. doi: 10.4103/JPBS.JPBS_83_18. Review. PubMed PMID: 30568374; PubMed Central PMCID: PMC6266642.

11: Bhat NA, Hamdani AM, Masoodi FA. Development of functional cookies using saffron extract. J Food Sci Technol. 2018 Dec;55(12):4918-4927. doi: 10.1007/s13197-018-3426-1. Epub 2018 Oct 27. PubMed PMID: 30482987; PubMed Central PMCID: PMC6233447.

12: Kyriakoudi A, Tsimidou MZ. Properties of encapsulated saffron extracts in maltodextrin using the Büchi B-90 nano spray-dryer. Food Chem. 2018 Nov 15;266:458-465. doi: 10.1016/j.foodchem.2018.06.038. Epub 2018 Jun 14. PubMed PMID: 30381212.

13: 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. PubMed PMID: 30358226.

14: Karkoula E, Angelis A, Koulakiotis NS, Gikas E, Halabalaki M, Tsarbopoulos A, Skaltsounis AL. Rapid isolation and characterization of crocins, picrocrocin, and crocetin from saffron using centrifugal partition chromatography and LC-MS. J Sep Sci. 2018 Nov;41(22):4105-4114. doi: 10.1002/jssc.201800516. Epub 2018 Oct 10. PubMed PMID: 30232839.

15: Lamari FN, Papasotiropoulos V, Tsiris D, Bariamis SE, Sotirakis K, Pitsi E, Vogiatzoglou AP, Iatrou G. Phytochemical and genetic characterization of styles of wild Crocus species from the island of Crete, Greece and comparison to those of cultivated C. sativus. Fitoterapia. 2018 Oct;130:225-233. doi: 10.1016/j.fitote.2018.09.003. Epub 2018 Sep 10. PubMed PMID: 30213756.

16: Leone S, Recinella L, Chiavaroli A, Orlando G, Ferrante C, Leporini L, Brunetti L, Menghini L. Phytotherapic use of the Crocus sativus L. (Saffron) and its potential applications: A brief overview. Phytother Res. 2018 Dec;32(12):2364-2375. doi: 10.1002/ptr.6181. Epub 2018 Aug 22. PubMed PMID: 30136324.

17: Alemzadeh E, Oryan A. Effectiveness of a Crocus sativus Extract on Burn Wounds in Rats. Planta Med. 2018 Nov;84(16):1191-1200. doi: 10.1055/a-0631-3620. Epub 2018 May 23. PubMed PMID: 29791931.

18: Khorasanchi Z, Shafiee M, Kermanshahi F, Khazaei M, Ryzhikov M, Parizadeh MR, Kermanshahi B, Ferns GA, Avan A, Hassanian SM. Crocus sativus a natural food coloring and flavoring has potent anti-tumor properties. Phytomedicine. 2018 Apr 1;43:21-27. doi: 10.1016/j.phymed.2018.03.041. Epub 2018 Mar 19. Review. PubMed PMID: 29747750.

19: Akbari G, Ali Mard S, Veisi A. A comprehensive review on regulatory effects of crocin on ischemia/reperfusion injury in multiple organs. Biomed Pharmacother. 2018 Mar;99:664-670. doi: 10.1016/j.biopha.2018.01.113. Epub 2018 Feb 20. Review. PubMed PMID: 29710463.

20: Moras B, Loffredo L, Rey S. Quality assessment of saffron (Crocus sativus L.) extracts via UHPLC-DAD-MS analysis and detection of adulteration using gardenia fruit extract (Gardenia jasminoides Ellis). Food Chem. 2018 Aug 15;257:325-332. doi: 10.1016/j.foodchem.2018.03.025. Epub 2018 Mar 8. PubMed PMID: 29622218.