Safflower red
featured

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

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

img
Safflower red
CAS# 36338-96-2

Theoretical Analysis

MedKoo Cat#: 598948
Name: Safflower red
CAS#: 36338-96-2
Chemical Formula: C43H42O22
Exact Mass: 910.22
Molecular Weight: 910.780
Elemental Analysis: C, 56.71; H, 4.65; O, 38.65

Price and Availability

Size Price Availability Quantity
5g USD 350 2 Weeks
10g USD 550 2 Weeks
25g USD 950 2 Weeks
Bulk inquiry

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: color value 30 (E1%,1cm,5) (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, DMF, and PBS (pH 7.2)

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

More Info:

Product Data:
Biological target: Safflower red, at concentrations of 100 and 200 µM, counteracts the effects of LPS on collagen II, aggrecan levels, and TNF expression in rat nucleus pulposus cells. In a rat model of cerebral ischemia-reperfusion injury, a dose of 40 mg/kg of safflower red reverses changes in serum GSH, SOD, and MDA levels, reducing infarct area and brain edema induced by MCAO.
In vitro activity: Safflower red may be a potential therapeutic drug for the treatment of intervertebral disc degeneration. In this study, a protective effect of safflower red on cultured rat nucleus pulposus cells was observed against lipopolysaccharide-induced matrix degradation and inflammation. Pretreatment with safflower red significantly suppressed lipopolysaccharide-induced activation of the MAPK pathway. Reference: Exp Ther Med. 2017 Aug;14(2):1614-1620. https://pubmed.ncbi.nlm.nih.gov/28810627/
In vivo activity: Safflower red treatment improved outcomes in middle cerebral artery occlusion rats, reducing neurological deficits, brain water content, and infarct size while increasing MAP-2 immunoreactivity in the cortex. Safflower red suppressed the cortex NF-κB/NLRP3 inflammasome pathway, lowered serum TNF-α, IL-1β, and IL-6 levels, and inhibited Fe2+ and ROS accumulation. It restored several protein expression levels in the brain. Safflower red reversed serum glutathione, superoxide dismutase, and malondialdehyde levels. Reference: Int J Mol Med. 2021 Apr;47(4):52. https://pubmed.ncbi.nlm.nih.gov/33576458/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 1.0 1.10
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
Formulation protocol: 1. Chen B, Wang HT, Yu B, Zhang JD, Feng Y. Carthamin yellow inhibits matrix degradation and inflammation induced by LPS in the intervertebral disc via suppression of MAPK pathway activation. Exp Ther Med. 2017 Aug;14(2):1614-1620. doi: 10.3892/etm.2017.4645. Epub 2017 Jun 22. PMID: 28810627; PMCID: PMC5525633. 2. Guo H, Zhu L, Tang P, Chen D, Li Y, Li J, Bao C. Carthamin yellow improves cerebral ischemia‑reperfusion injury by attenuating inflammation and ferroptosis in rats. Int J Mol Med. 2021 Apr;47(4):52. doi: 10.3892/ijmm.2021.4885. Epub 2021 Feb 12. PMID: 33576458; PMCID: PMC7895518.
In vitro protocol: 1. Chen B, Wang HT, Yu B, Zhang JD, Feng Y. Carthamin yellow inhibits matrix degradation and inflammation induced by LPS in the intervertebral disc via suppression of MAPK pathway activation. Exp Ther Med. 2017 Aug;14(2):1614-1620. doi: 10.3892/etm.2017.4645. Epub 2017 Jun 22. PMID: 28810627; PMCID: PMC5525633.
In vivo protocol: 1. Guo H, Zhu L, Tang P, Chen D, Li Y, Li J, Bao C. Carthamin yellow improves cerebral ischemia‑reperfusion injury by attenuating inflammation and ferroptosis in rats. Int J Mol Med. 2021 Apr;47(4):52. doi: 10.3892/ijmm.2021.4885. Epub 2021 Feb 12. PMID: 33576458; PMCID: PMC7895518.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.