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

Hodoodo CAT#: H558527

CAS#: 77-95-2

Description: 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

Instruction

Theoretical Analysis

Hodoodo Cat#: H558527
Name: Quinic acid
CAS#: 77-95-2
Chemical Formula: C7H12O6
Exact Mass: 192.06
Molecular Weight: 192.170
Elemental Analysis: C, 43.75; H, 6.29; O, 49.95

Price and Availability

Size	Price	Availability
25g	USD 240	2 Weeks
100g	USD 490	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. Hodoodo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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:
In vitro protocol:
In vivo protocol:

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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

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