Cryptochlorogenic acid | CAS# 905-99-7 | allergenic

MedKoo Cat#: 574453 | Name: Cryptochlorogenic acid

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Description:

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

Cryptochlorogenic acid is a phenolic acid that inhibits rat lens aldose reductase (RLAR) in vitro, inhibits the growth of S. aureus, and scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals in a cell-free assay. Cryptochlorogenic acid is allergenic, inducing degranulation of RBL-2H3 mast cells in vitro and increasing plasma serotonin and β-hexosaminidase levels in guinea pigs in vivo.

Chemical Structure

Cryptochlorogenic acid

CAS#905-99-7

Theoretical Analysis

MedKoo Cat#: 574453

Name: Cryptochlorogenic acid

CAS#: 905-99-7

Chemical Formula: C16H18O9

Exact Mass: 354.0951

Molecular Weight: 354.31

Elemental Analysis: C, 54.24; H, 5.12; O, 40.64

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks
50mg	USD 1,050.00	2 Weeks

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Synonym

4-O-Caffeoylquinic Acid; Cryptochlorogenic acid; 4-Caffeoylquinic acid; 4-Cqa

IUPAC/Chemical Name

(1alpha,3R,4alpha,5R)-4-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acid

InChi Key

GYFFKZTYYAFCTR-JUHZACGLSA-N

InChi Code

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

SMILES Code

O=C(O)[C@@]1(O)C[C@@H](O)[C@H](OC(/C=C/C2=CC(O)=C(O)C=C2)=O)[C@H](O)C1

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Cryptochlorogenic acid is a natural product.

In vitro activity:

The results revealed that CCGA (cryptochlorogenic acid) dose-dependently inhibited LPS-induced production of NO, TNF-α, and IL-6 and blocked iNOS, COX-2, TNF-α, and IL-6 expressions. CCGA also significantly increased the GSH/GSSG ratio and SOD activity and reduced the MDA level. Moreover, CCGA suppressed the nuclear translocation of NF-κB by hindering the phosphorylation of IκB kinase (IKK) and degrading IκB. It also downregulated the phosphorylation of MAPKs. Reference: Int Immunopharmacol. 2020 Jun;83:106436. https://pubmed.ncbi.nlm.nih.gov/32234671/

In vivo activity:

The GSH, GSH/GSSG and GPX4 were all reduced in the model group when compared with control and the levels of these anti-oxidant indicators in rats with diabetes were further increased by CCA (cryptochlorogenic acid) in a concentration-dependent manner (Figure 4A–C). As indicated by the data, the CCA at high concentrations has better enhanced anti-oxidant effects than RH. Reference: Diabetes Metab Syndr Obes. 2020; 13: 1921–1931. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7294720/

	Solvent	mg/mL	mM
Solubility
	DMSO	57.0	160.88
	DMF	71.0	200.39
	Ethanol	25.0	70.56
	PBS (pH 7.2)	25.0	70.56

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 354.31 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.

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. Zhou Y. The Protective Effects of Cryptochlorogenic Acid on β-Cells Function in Diabetes in vivo and vitro via Inhibition of Ferroptosis. Diabetes Metab Syndr Obes. 2020 Jun 8;13:1921-1931. doi: 10.2147/DMSO.S249382. PMID: 32606852; PMCID: PMC7294720. 2. Zhao XL, Yu L, Zhang SD, Ping K, Ni HY, Qin XY, Zhao CJ, Wang W, Efferth T, Fu YJ. Cryptochlorogenic acid attenuates LPS-induced inflammatory response and oxidative stress via upregulation of the Nrf2/HO-1 signaling pathway in RAW 264.7 macrophages. Int Immunopharmacol. 2020 Jun;83:106436. doi: 10.1016/j.intimp.2020.106436. Epub 2020 Mar 29. PMID: 32234671.

In vitro protocol:

In vivo protocol:

1: Li J, Chen X, Li X, Tang J, Li Y, Liu B, Guo S. Cryptochlorogenic acid and its metabolites ameliorate myocardial hypertrophy through a HIF1α-related pathway. Food Funct. 2022 Feb 21;13(4):2269-2282. doi: 10.1039/d1fo03838a. PMID: 35141734. 2: Zhao XL, Yu L, Zhang SD, Ping K, Ni HY, Qin XY, Zhao CJ, Wang W, Efferth T, Fu YJ. Cryptochlorogenic acid attenuates LPS-induced inflammatory response and oxidative stress via upregulation of the Nrf2/HO-1 signaling pathway in RAW 264.7 macrophages. Int Immunopharmacol. 2020 Jun;83:106436. doi: 10.1016/j.intimp.2020.106436. Epub 2020 Mar 29. PMID: 32234671. 3: Ma X, Okyere SK, Hu L, Wen J, Ren Z, Deng J, Hu Y. Anti-Inflammatory Activity and Mechanism of Cryptochlorogenic Acid from Ageratina adenophora. Nutrients. 2022 Jan 19;14(3):439. doi: 10.3390/nu14030439. PMID: 35276797; PMCID: PMC8839916. 4: Li J, Wang SP, Wang YQ, Shi L, Zhang ZK, Dong F, Li HR, Zhang JY, Man YQ. Comparative metabolism study on chlorogenic acid, cryptochlorogenic acid and neochlorogenic acid using UHPLC-Q-TOF MS coupled with network pharmacology. Chin J Nat Med. 2021 Mar;19(3):212-224. doi: 10.1016/S1875-5364(21)60023-7. PMID: 33781455. 5: Wang Y, Wen J, Zheng W, Zhao L, Fu X, Wang Z, Xiong Z, Li F, Xiao W. Simultaneous determination of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and geniposide in rat plasma by UPLC-MS/MS and its application to a pharmacokinetic study after administration of Reduning injection. Biomed Chromatogr. 2015 Jan;29(1):68-74. doi: 10.1002/bmc.3241. Epub 2014 May 20. PMID: 24842397. 6: Zhou Y. The Protective Effects of Cryptochlorogenic Acid on β-Cells Function in Diabetes in vivo and vitro via Inhibition of Ferroptosis. Diabetes Metab Syndr Obes. 2020 Jun 8;13:1921-1931. doi: 10.2147/DMSO.S249382. PMID: 32606852; PMCID: PMC7294720. 7: Chen X, Kang F, Lai J, Deng X, Guo X, Liu S. Comparative effectiveness of phlegm-heat clearing Chinese medicine injections for AECOPD: A systematic review and network meta-analysis. J Ethnopharmacol. 2022 Jun 28;292:115043. doi: 10.1016/j.jep.2022.115043. Epub 2022 Feb 4. PMID: 35124185. 8: Zhu P, Miao XL, Chen Y. [Degradation kinetics of chlorogenic acid, cryptochlorogenic acid, and neochlorogenic acid at neutral and alkaline pH values]. Yao Xue Xue Bao. 2016 Jan;51(1):122-6. Chinese. PMID: 27405173. 9: Wang J, Zhang X, Wu X, Zhao X, Di L, Guo Q, Wang S. [Simultaneous determination of chlorogenic acid, cryptochlorogenic acid, caffeic acid, naringin, hesperidin and linarin in xiao'erjinning oral liquid by an HPLC method]. Zhongguo Zhong Yao Za Zhi. 2010 Jul;35(13):1702-5. Chinese. doi: 10.4268/cjcmm20101311. PMID: 20862961. 10: Li L, Chen B, An T, Zhang H, Xia B, Li R, Zhu R, Tian Y, Wang L, Zhao D, Mo F, Li Y, Yang G, Orekhov AN, Prentki M, Zhang D, Jiang G, Zhu X. BaZiBuShen alleviates altered testicular morphology and spermatogenesis and modulates Sirt6/P53 and Sirt6/NF-κB pathways in aging mice induced by D-galactose and NaNO2. J Ethnopharmacol. 2021 May 10;271:113810. doi: 10.1016/j.jep.2021.113810. Epub 2021 Jan 26. PMID: 33508368. 11: Yang Y, Wei Q, An R, Zhang HM, Shen JY, Qin XY, Han XL, Li J, Li XW, Gao XM, He J, Mao HP. Anti-osteoporosis effect of Semen Cuscutae in ovariectomized mice through inhibition of bone resorption by osteoclasts. J Ethnopharmacol. 2022 Mar 1;285:114834. doi: 10.1016/j.jep.2021.114834. Epub 2021 Nov 18. PMID: 34801609. 12: Haghi G, Hatami A, Mehran M, Hosseini H. Caffeic acid derivatives from Bupleurum chinense. Res Pharm Sci. 2014 Sep-Oct;9(5):323-30. PMID: 25657804; PMCID: PMC4318000. 13: Chen L, Li J, Zhu Y, Guo L, Ji R, Miao Y, Guo L, Du H, Liu D. Caffeic Acid, an Allelochemical in Artemisia argyi, Inhibits Weed Growth via Suppression of Mitogen-Activated Protein Kinase Signaling Pathway and the Biosynthesis of Gibberellin and Phytoalexin. Front Plant Sci. 2022 Jan 6;12:802198. doi: 10.3389/fpls.2021.802198. PMID: 35069660; PMCID: PMC8770944. 14: Ianni F, Barola C, Blasi F, Moretti S, Galarini R, Cossignani L. Investigation on chlorogenic acid stability in aqueous solution after microwave treatment. Food Chem. 2022 Apr 16;374:131820. doi: 10.1016/j.foodchem.2021.131820. Epub 2021 Dec 9. PMID: 35021582. 15: Choi WG, Kim JH, Kim DK, Lee Y, Yoo JS, Shin DH, Lee HS. Simultaneous Determination of Chlorogenic Acid Isomers and Metabolites in Rat Plasma Using LC-MS/MS and Its Application to A Pharmacokinetic Study Following Oral Administration of Stauntonia Hexaphylla Leaf Extract (YRA-1909) to Rats. Pharmaceutics. 2018 Sep 2;10(3):143. doi: 10.3390/pharmaceutics10030143. PMID: 30200538; PMCID: PMC6161084. 16: Tan Y, Xu S, Zhang H, Tang H, Wang Z, Li J, Tan N. A comprehensive quality evaluation strategy of Mailuoning oral liquid based on fingerprint, qualitative and quantitative analyses. J Pharm Biomed Anal. 2023 Sep 20;234:115497. doi: 10.1016/j.jpba.2023.115497. Epub 2023 May 30. PMID: 37573813. 17: Zhou W, Shan J, Wang S, Ju W, Meng M, Cai B, Di L. Simultaneous determination of caffeic acid derivatives by UPLC-MS/MS in rat plasma and its application in pharmacokinetic study after oral administration of Flos Lonicerae-Fructus Forsythiae herb combination. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Feb 15;949-950:7-15. doi: 10.1016/j.jchromb.2013.12.035. Epub 2014 Jan 7. PMID: 24441018. 18: Xie W, Yu Y, Hou M, Zhang Y, Yu H, Zhang H, Zhang G, Jing H, Chen A. Simultaneous separation and determination of five chlorogenic acid isomers in Honeysuckle by capillary electrophoresis using self-synthesized ionic liquid [N-methylimidazole-β-cyclodextrin] [bromide] as separation selector. J Sep Sci. 2022 Aug;45(16):3197-3207. doi: 10.1002/jssc.202200352. Epub 2022 Jul 12. PMID: 35772030. 19: Xu Z, Cao Q, Manyande A, Xiong S, Du H. Analysis of the binding selectivity and inhibiting mechanism of chlorogenic acid isomers and their interaction with grass carp endogenous lipase using multi-spectroscopic, inhibition kinetics and modeling methods. Food Chem. 2022 Jul 15;382:132106. doi: 10.1016/j.foodchem.2022.132106. Epub 2022 Jan 10. PMID: 35240531. 20: Ji X, Wang B, Paudel YN, Li Z, Zhang S, Mou L, Liu K, Jin M. Protective Effect of Chlorogenic Acid and Its Analogues on Lead-Induced Developmental Neurotoxicity Through Modulating Oxidative Stress and Autophagy. Front Mol Biosci. 2021 Jun 11;8:655549. doi: 10.3389/fmolb.2021.655549. PMID: 34179077; PMCID: PMC8226318.