Safflower red
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MedKoo CAT#: 598948

CAS#: 36338-96-2

Description: Safflower red is a polyketide synthase-derived quinochalcone glucoside red pigment originally isolated from C. tinctorius that has diverse biological activities. Safflower red (100 and 200 µM) inhibits LPS-induced decreases in collagen II and aggrecan levels and reverses LPS-induced increases in TNF expression in isolated rat nucleus pulposus cells. It reverses decreases in serum glutathione (GSH) and superoxide dismutase (SOD) levels and increases in serum malondialdehyde (MDA) levels, as well as decreases infarct area and brain edema induced by middle cerebral artery occlusion (MCAO), in a rat model of cerebral ischemia-reperfusion injury when administered at a dose of 40 mg/kg. Formulations containing safflower red have been used in the food, cosmetics, and clothing industries.


Chemical Structure

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Safflower red
CAS# 36338-96-2

Theoretical Analysis

MedKoo Cat#: 598948
Name: Safflower red
CAS#: 36338-96-2
Chemical Formula: C43H42O22
Exact Mass: 910.2168
Molecular Weight: 910.78
Elemental Analysis: C, 56.71; H, 4.65; O, 38.65

Price and Availability

Size Price Availability Quantity
5.0g USD 210.0 2 Weeks
10.0g USD 340.0 2 Weeks
25.0g USD 540.0 2 Weeks
50.0g USD 810.0 2 Weeks
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Synonym: Carthamin; Carthamin Yellow; Natural Red 26; Liofresh Red CR; Safflower red;

IUPAC/Chemical Name: (E)-5,6-dihydroxy-4-((E)-3-(4-hydroxyphenyl)acryloyl)-2-((2,3,4-trihydroxy-5-((E)-3-(4-hydroxyphenyl)acryloyl)-6-oxo-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)cyclohexa-1,4-dien-1-yl)methylene)-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)cyclohex-4-ene-1,3-dione

InChi Key: WLYGSPLCNKYESI-HTALNNRZSA-N

InChi Code: InChI=1S/C43H42O22/c44-14-24-30(52)32(54)34(56)40(64-24)42(62)36(58)20(28(50)26(38(42)60)22(48)11-5-16-1-7-18(46)8-2-16)13-21-29(51)27(23(49)12-6-17-3-9-19(47)10-4-17)39(61)43(63,37(21)59)41-35(57)33(55)31(53)25(15-45)65-41/h1-13,24-25,30-35,40-41,44-47,52-58,60-63H,14-15H2/b11-5+,12-6+,21-13+/t24-,25-,30-,31-,32+,33+,34-,35-,40-,41-,42?,43?/m1/s1

SMILES Code: O=C1/C(C(C(C(/C=C/C2=CC=C(O)C=C2)=O)=C(O)C1([C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)=O)=C/C4=C(O)C(O)([C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)C(O)=C(C(/C=C/C6=CC=C(O)C=C6)=O)C4=O

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: 2934.99.03.00

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 1.0 1.1
DMSO 5.0 5.49
PBS (pH 7.2) 10.0 10.98

Preparing Stock Solutions

The following data is based on the product molecular weight 910.78 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

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1: Yoshida T, Terasaka K, Kato S, Bai F, Sugimoto N, Akiyama H, Yamazaki T, Mizukami H. Quantitative Determination of Carthamin in Carthamus Red by 1H-NMR Spectroscopy. Chem Pharm Bull (Tokyo). 2013;61(12):1264-8. PubMed PMID: 24436958.

2: Salem N, Msaada K, Elkahoui S, Mangano G, Azaeiz S, Ben Slimen I, Kefi S, Pintore G, Limam F, Marzouk B. Evaluation of antibacterial, antifungal, and antioxidant activities of safflower natural dyes during flowering. Biomed Res Int. 2014;2014:762397. doi: 10.1155/2014/762397. Epub 2014 Jun 22. PubMed PMID: 25045699; PubMed Central PMCID: PMC4090561.

3: Dai Y, Witkamp GJ, Verpoorte R, Choi YH. Tailoring properties of natural deep eutectic solvents with water to facilitate their applications. Food Chem. 2015 Nov 15;187:14-9. doi: 10.1016/j.foodchem.2015.03.123. Epub 2015 Apr 3. PubMed PMID: 25976992.

4: Hiramatsu M, Takahashi T, Komatsu M, Kido T, Kasahara Y. Antioxidant and neuroprotective activities of Mogami-benibana (safflower, Carthamus tinctorius Linne). Neurochem Res. 2009 Apr;34(4):795-805. doi: 10.1007/s11064-008-9884-5. Epub 2008 Dec 12. PubMed PMID: 19082884.

5: SHIMOKORIYAMA M, HATTORI S. On the formation of carthamin in the flowers of Carthamus tinctorius. Arch Biochem Biophys. 1955 Jan;54(1):93-101. PubMed PMID: 13229360.

6: Cho MH, Paik YS, Hahn TR. Enzymatic conversion of precarthamin to carthamin by a purified enzyme from the yellow petals of safflower. J Agric Food Chem. 2000 Sep;48(9):3917-21. PubMed PMID: 10995291.

7: Kim JB, Paik YS. Stability of carthamin fromCarthamus tinctorius in aqueous solution: pH and temperature effects. Arch Pharm Res. 1997 Dec;20(6):643-6. doi: 10.1007/BF02975225. PubMed PMID: 18982273.

8: Asgarpanah J, Kazemivash N. Phytochemistry, pharmacology and medicinal properties of Carthamus tinctorius L. Chin J Integr Med. 2013 Feb;19(2):153-9. doi: 10.1007/s11655-013-1354-5. Epub 2013 Jan 31. Review. PubMed PMID: 23371463.

9: Zhu M, Guo Z. [Determination of the saflor yellow-A in Carthamin tinctorius]. Zhong Yao Cai. 2000 Aug;23(8):458-9. Chinese. PubMed PMID: 12575160.

10: Nakano K, Sekino Y, Yomo N, Wakayama S, Miyano S, Kusaka K, Daimon E, Imaizumi K, Totsuka Y, Oda S, et al. High-performance liquid chromatography of carthamin, safflor yellow A and a precursor of carthamin. Application to the investigation of an unknown red pigment produced in cultured cells of safflower. J Chromatogr. 1988 Apr 1;438(1):61-72. PubMed PMID: 3379118.

11: Sato K, Sugimoto N, Ohta M, Yamazaki T, Maitani T, Tanamoto K. Structure determination of minor red pigment in carthamus red colorant isolated by preparative LC/MS. Food Addit Contam. 2003 Nov;20(11):1015-22. PubMed PMID: 14668152.

12: Dai Y, Verpoorte R, Choi YH. Natural deep eutectic solvents providing enhanced stability of natural colorants from safflower (Carthamus tinctorius). Food Chem. 2014 Sep 15;159:116-21. doi: 10.1016/j.foodchem.2014.02.155. Epub 2014 Mar 10. PubMed PMID: 24767033.

13: Cho MH, Hahn TR. Purification and characterization of precarthamin decarboxylase from the yellow petals of Carthamus tinctorius L. Arch Biochem Biophys. 2000 Oct 15;382(2):238-44. PubMed PMID: 11068875.

14: He J, Li S, Xu K, Tang B, Yang H, Wang Q, Li H. Binding properties of the natural red dye carthamin with human serum albumin: Surface plasmon resonance, isothermal titration microcalorimetry, and molecular docking analysis. Food Chem. 2017 Apr 15;221:650-656. doi: 10.1016/j.foodchem.2016.11.124. Epub 2016 Nov 23. PubMed PMID: 27979254.

15: Li Y, Che Q. [Studies on chemical components of Carthamus tinctorius petals]. Yao Xue Xue Bao. 1998 Aug;33(8):626-8. Chinese. PubMed PMID: 12016905.

16: Meselhy MR, Kadota S, Momose Y, Hatakeyama N, Kusai A, Hattori M, Namba T. Two new quinochalcone yellow pigments from Carthamus tinctorius and Ca2+ antagonistic activity of tinctormine. Chem Pharm Bull (Tokyo). 1993 Oct;41(10):1796-802. PubMed PMID: 8281577.

17: Tu Y, Liu F, Guo D, Fan L, Zhu Z, Xue Y, Gao Y, Guo M. Molecular characterization of flavanone 3-hydroxylase gene and flavonoid accumulation in two chemotyped safflower lines in response to methyl jasmonate stimulation. BMC Plant Biol. 2016 Jun 10;16(1):132. doi: 10.1186/s12870-016-0813-5. PubMed PMID: 27286810; PubMed Central PMCID: PMC4902928.

18: Hayashi T, Ohmori K, Suzuki K. Synthetic Study on Carthamin. 2. Stereoselective Approach to C-Glycosyl Quinochalcone via Desymmetrization. Org Lett. 2017 Feb 17;19(4):866-869. doi: 10.1021/acs.orglett.6b03899. Epub 2017 Feb 6. PubMed PMID: 28165754.

19: Kazuma K, Takahashi T, Sato K, Takeuchi H, Matsumoto T, Okuno T. Quinochalcones and flavonoids from fresh florets in different cultivars of Carthamus tinctorius L. Biosci Biotechnol Biochem. 2000 Aug;64(8):1588-99. PubMed PMID: 10993143.

20: Gu H, Ma L, Yuan B, Zhang YL, Wang Y, Qiao YJ. [Analysis on anti-hepatoma effect of medicine invigorating blood circulation and eliminating blood stasis based on warm-pungent-liver efficiency network]. Zhongguo Zhong Yao Za Zhi. 2014 Jul;39(13):2417-21. Chinese. PubMed PMID: 25276956.

Safflower red

100.0mg / Not available