Quinic acid | CAS#77-95-2 | metabolite

MedKoo Cat#: 558527 | Name: Quinic acid

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Description:

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

Quinic acid is metabolite related to the shikimate pathway in plants and microorganisms. It is a valuable chiral synthon. Quinic acid has been isolated previously from cinchona bark.

Chemical Structure

Quinic acid

CAS#77-95-2

Theoretical Analysis

MedKoo Cat#: 558527

Name: Quinic acid

CAS#: 77-95-2

Chemical Formula: C7H12O6

Exact Mass: 192.0600

Molecular Weight: 192.17

Elemental Analysis: C, 43.75; H, 6.29; O, 49.95

Price and Availability

Size	Price	Availability	Quantity
25g	USD 240.00
100g	USD 490.00

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Related CAS #

No Data

Synonym

Quinic acid; Kinic acid; Chinic acid;

IUPAC/Chemical Name

Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (-)-

InChi Key

AAWZDTNXLSGCEK-UHFFFAOYSA-N

InChi Code

InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)

SMILES Code

O=C(C1(O)CC(O)C(O)C(O)C1)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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Quinic acid exhibits various biological activities, such as antioxidant, antidiabetic, anticancer activity, antimicrobial, antiviral, aging, protective, anti-nociceptive and analgesic effects.

In vitro activity:

In this study, a dental membrane scaffold was fabricated using a 3D printing technique, and the antimicrobial effect of pomegranate seed and peel extract were investigated. The addition of pomegranate seed and peel extracts into the scaffolds resulted in a significant antimicrobial effect on S. aureus and E. faecalis bacteria. One of the components of interest in pomegranate seed and peel extracts was quinic acid, implying that quinic acid may have antimicrobial effects. Reference : Pharmaceutics. 2023 Feb 22;15(3):737. https://pubmed.ncbi.nlm.nih.gov/36986598/

In vivo activity:

Tetrastigma hemsleyanum is an economically and medicinally valuable species. However, the material basis of its pharmacological action and the biomarkers associated with its anti-cancer and anti-inflammatory effects are unclear. One of its compounds, quinic acid, is associated with anticancer activity and anti-inflammatory activity. Reference: Molecules. 2023 Mar 28;28(7):3021. https://pubmed.ncbi.nlm.nih.gov/37049789/

	Solvent	mg/mL	mM
Solubility
	DMSO	38.0	197.74

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 192.17 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. Matos da Silva M, Pereira Alexandre G, Magalhães MR, Torres AM, Kato L, Costa da Silva V, Teixeira de Saboia Morais SM, Garcia Rodriguez A, Pacheco Fill T, Pereira AK, Roque J, Souza Simão JL, Pasqualotto Severino VG. Musa spp. cultivars as a neutralising source against some toxic activities of Bothrops and Crotalus genus snake venoms. Toxicon. 2023 Jun 1;228:107106. doi: 10.1016/j.toxicon.2023.107106. Epub 2023 Apr 7. PMID: 37031872. 2. Karabulut H, Ulag S, Dalbayrak B, Arisan ED, Taskin T, Guncu MM, Aksu B, Valanezhad A, Gunduz O. A Novel Approach for the Fabrication of 3D-Printed Dental Membrane Scaffolds including Antimicrobial Pomegranate Extract. Pharmaceutics. 2023 Feb 22;15(3):737. doi: 10.3390/pharmaceutics15030737. PMID: 36986598; PMCID: PMC10054296. 3. Eruygur N, Buyukyildirim T, Tetik Rama S, Ayaz F, Tekin M, Tuzcu M, Akcakavak G, Abdullah Yilmaz M. Phytochemical Profiling and Biological Activity of Achillea sintenisii Hub.-Mor. Chem Biodivers. 2023 May 19:e202201258. doi: 10.1002/cbdv.202201258. Epub ahead of print. PMID: 37203434. 4. Xia J, Li X, Lin M, Yu J, Zeng Z, Ye F, Hu G, Miu Q, He Q, Zhang X, Liang Z. Screening out Biomarkers of Tetrastigma hemsleyanum for Anti-Cancer and Anti-Inflammatory Based on Spectrum-Effect Relationship Coupled with UPLC-Q-TOF-MS. Molecules. 2023 Mar 28;28(7):3021. doi: 10.3390/molecules28073021. PMID: 37049789; PMCID: PMC10096277.

In vitro protocol:

In vivo protocol:

1. Eruygur N, Buyukyildirim T, Tetik Rama S, Ayaz F, Tekin M, Tuzcu M, Akcakavak G, Abdullah Yilmaz M. Phytochemical Profiling and Biological Activity of Achillea sintenisii Hub.-Mor. Chem Biodivers. 2023 May 19:e202201258. doi: 10.1002/cbdv.202201258. Epub ahead of print. PMID: 37203434. 2. Xia J, Li X, Lin M, Yu J, Zeng Z, Ye F, Hu G, Miu Q, He Q, Zhang X, Liang Z. Screening out Biomarkers of Tetrastigma hemsleyanum for Anti-Cancer and Anti-Inflammatory Based on Spectrum-Effect Relationship Coupled with UPLC-Q-TOF-MS. Molecules. 2023 Mar 28;28(7):3021. doi: 10.3390/molecules28073021. PMID: 37049789; PMCID: PMC10096277.

1: Liu Z, Feng Z, Yang Y, Jiang J, Zhang P. Acyl quinic acid derivatives from the stems of Erycibe obtusifolia. Fitoterapia. 2014 Dec;99:109-16. doi: 10.1016/j.fitote.2014.09.012. Epub 2014 Sep 22. PubMed PMID: 25256062. 2: Zanello PR, Koishi AC, Rezende Júnior Cde O, Oliveira LA, Pereira AA, de Almeida MV, Duarte dos Santos CN, Bordignon J. Quinic acid derivatives inhibit dengue virus replication in vitro. Virol J. 2015 Dec 22;12:223. doi: 10.1186/s12985-015-0443-9. PubMed PMID: 26695767; PubMed Central PMCID: PMC4688969. 3: Thompson KE, Zeng K, Wilson CM, Gaber MW, Miller DD, Yates CR. Quinic acid derivative KZ-41 exhibits radiomitigating activity in preclinical models of radiation injury. Drug Dev Res. 2014 Feb;75(1):29-36. doi: 10.1002/ddr.21164. Epub 2013 Dec 26. PubMed PMID: 24648047. 4: Zhang M, Liu WX, Zheng MF, Xu QL, Wan FH, Wang J, Lei T, Zhou ZY, Tan JW. Bioactive quinic acid derivatives from Ageratina adenophora. Molecules. 2013 Nov 14;18(11):14096-104. doi: 10.3390/molecules181114096. PubMed PMID: 24241153. 5: Lee SY, Moon E, Kim SY, Lee KR. Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia. Bioorg Med Chem Lett. 2013 Apr 1;23(7):2140-4. doi: 10.1016/j.bmcl.2013.01.115. Epub 2013 Feb 8. PubMed PMID: 23462643. 6: Deshpande S, Matei MF, Jaiswal R, Bassil BS, Kortz U, Kuhnert N. Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid. J Agric Food Chem. 2016 Sep 28;64(38):7298-306. doi: 10.1021/acs.jafc.6b02472. Epub 2016 Sep 14. PubMed PMID: 27513177. 7: Yang YJ, Liu X, Wu HR, He XF, Bi YR, Zhu Y, Liu ZL. Radical scavenging activity and cytotoxicity of active quinic acid derivatives from Scorzonera divaricata roots. Food Chem. 2013 Jun 1;138(2-3):2057-63. doi: 10.1016/j.foodchem.2012.10.122. Epub 2012 Nov 21. PubMed PMID: 23411343. 8: Peng Y, Dong Y, Mahato RI. Synthesis and Characterization of a Novel Mycophenolic Acid-Quinic Acid Conjugate Serving as Immunosuppressant with Decreased Toxicity. Mol Pharm. 2015 Dec 7;12(12):4445-53. doi: 10.1021/acs.molpharmaceut.5b00639. Epub 2015 Nov 11. PubMed PMID: 26529468. 9: Rezende CO Jr, Oliveira LA, Oliveira BA, Almeida CG, Ferreira BS, Le Hyaric M, Carvalho GS, Lourenço MC, Batista M, Marchini FK, Silva VL, Diniz CG, Almeida MV. Synthesis and Antibacterial Activity of Alkylated Diamines and Amphiphilic Amides of Quinic Acid Derivatives. Chem Biol Drug Des. 2015 Sep;86(3):344-50. doi: 10.1111/cbdd.12498. Epub 2015 Jan 20. PubMed PMID: 25528858. 10: Toutounchian JJ, Steinle JJ, Makena PS, Waters CM, Wilson MW, Haik BG, Miller DD, Yates CR. Modulation of radiation injury response in retinal endothelial cells by quinic acid derivative KZ-41 involves p38 MAPK. PLoS One. 2014 Jun 23;9(6):e100210. doi: 10.1371/journal.pone.0100210. eCollection 2014. PubMed PMID: 24956278; PubMed Central PMCID: PMC4067294. 11: Link LA, Lonnecker AT, Hearon K, Maher CA, Raymond JE, Wooley KL. Photo-cross-linked poly(thioether-co-carbonate) networks derived from the natural product quinic acid. ACS Appl Mater Interfaces. 2014 Oct 22;6(20):17370-5. doi: 10.1021/am506087e. Epub 2014 Oct 7. PubMed PMID: 25289727. 12: Engström MT, Pälijärvi M, Salminen JP. Rapid Fingerprint Analysis of Plant Extracts for Ellagitannins, Gallic Acid, and Quinic Acid Derivatives and Quercetin-, Kaempferol- and Myricetin-Based Flavonol Glycosides by UPLC-QqQ-MS/MS. J Agric Food Chem. 2015 Apr 29;63(16):4068-79. doi: 10.1021/acs.jafc.5b00595. Epub 2015 Apr 15. PubMed PMID: 25853372. 13: Suárez-Quiroz ML, Alonso Campos A, Valerio Alfaro G, González-Ríos O, Villeneuve P, Figueroa-Espinoza MC. Anti-Aspergillus activity of green coffee 5-O-caffeoyl quinic acid and its alkyl esters. Microb Pathog. 2013 Aug-Sep;61-62:51-6. doi: 10.1016/j.micpath.2013.05.005. Epub 2013 May 15. PubMed PMID: 23684728. 14: Kashiwada Y, Ahmed FA, Kurimoto S, Kim SY, Shibata H, Fujioka T, Takaishi Y. New α-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam. J Nat Med. 2012 Jan;66(1):217-21. doi: 10.1007/s11418-011-0563-5. Epub 2011 Jul 5. PubMed PMID: 21748486. 15: Chen J, Mangelinckx S, Ma L, Wang Z, Li W, De Kimpe N. Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast α-glucosidase and PTP1B inhibitory activity. Fitoterapia. 2014 Dec;99:1-6. doi: 10.1016/j.fitote.2014.08.015. Epub 2014 Aug 27. PubMed PMID: 25172103. 16: Zhang Q, Jiang Y, Toutounchian J, Wilson MW, Morales-Tirado V, Miller DD, Yates CR, Steinle JJ. Novel quinic acid derivative KZ-41 prevents retinal endothelial cell apoptosis without inhibiting retinoblastoma cell death through p38 signaling. Invest Ophthalmol Vis Sci. 2013 Sep 3;54(9):5937-43. doi: 10.1167/iovs.13-12326. PubMed PMID: 23942968; PubMed Central PMCID: PMC3762329. 17: Junior CO, Verde SC, Rezende CA, Caneschi W, Couri MR, McDougall BR, Robinson WE Jr, de Almeida MV. Synthesis and HIV-1 inhibitory activities of dicaffeoyl and digalloyl esters of quinic acid derivatives. Curr Med Chem. 2013;20(5):724-33. PubMed PMID: 23210852. 18: Besset CJ, Lonnecker AT, Streff JM, Wooley KL. Polycarbonates from the polyhydroxy natural product quinic acid. Biomacromolecules. 2011 Jul 11;12(7):2512-7. doi: 10.1021/bm2003048. Epub 2011 Jun 6. PubMed PMID: 21644574. 19: Pero RW, Lund H. Dietary quinic acid supplied as the nutritional supplement AIO + AC-11® leads to induction of micromolar levels of nicotinamide and tryptophan in the urine. Phytother Res. 2011 Jun;25(6):851-7. doi: 10.1002/ptr.3348. Epub 2010 Nov 22. PubMed PMID: 21104945. 20: Hagl S, Deusser H, Soyalan B, Janzowski C, Will F, Dietrich H, Albert FW, Rohner S, Richling E. Colonic availability of polyphenols and D-(-)-quinic acid after apple smoothie consumption. Mol Nutr Food Res. 2011 Mar;55(3):368-77. doi: 10.1002/mnfr.201000252. Epub 2010 Nov 9. PubMed PMID: 21370449. h