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MedKoo Cat#: 463045 | Name: Quillaic Acid
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Description:

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

Quillaic acid is a triterpene saponin that has been found in Q. saponaria bark and has diverse biological activities. It is cytotoxic to SNU-1 and KATO III gastric cancer cells. Quillaic acid induces hot plate analgesia in mice. It reduces ear edema induced by arachidonic acid or phorbol 12-myristate 13-acetate in mice when administered topically at doses of 0.7 and 1.6 mg/ear, respectively.

Chemical Structure

Quillaic Acid
Quillaic Acid
CAS#631-01-6

Theoretical Analysis

MedKoo Cat#: 463045

Name: Quillaic Acid

CAS#: 631-01-6

Chemical Formula: C30H46O5

Exact Mass: 486.3345

Molecular Weight: 486.69

Elemental Analysis: C, 74.04; H, 9.53; O, 16.44

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Quillaic Acid; Quillaja Sapogenin;
IUPAC/Chemical Name
(4aR,5R,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
InChi Key
MQUFAARYGOUYEV-UAWZMHPWSA-N
InChi Code
InChI=1S/C30H46O5/c1-25(2)13-14-30(24(34)35)19(15-25)18-7-8-21-26(3)11-10-22(32)27(4,17-31)20(26)9-12-28(21,5)29(18,6)16-23(30)33/h7,17,19-23,32-33H,8-16H2,1-6H3,(H,34,35)/t19-,20+,21+,22-,23+,26-,27-,28+,29+,30+/m0/s1
SMILES Code
OC([C@@]12[C@]([H])(C3=CC[C@]4([H])[C@]5(C)[C@@]([H])(CC[C@]4([C@]3(C)C[C@H]2O)C)[C@@]([C@@H](O)CC5)(C=O)C)CC(CC1)(C)C)=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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Quillaic acid is cytotoxic to SNU-1 and KATO III gastric cancer cells. Quillaic acid induces hot plate analgesia in mice. It reduces ear edema induced by arachidonic acid or phorbol 12-myristate 13-acetate in mice when administered topically at doses of 0.7 and 1.6 mg/ear, respectively.
In vitro activity:
Six undescribed triterpenoid saponins, named as hylomeconoside C-H, were isolated from the EtOH extract of Hylomecon japonica, two of which contain quillaic acid. 50% EtOH extract showed moderate inhibitory activity on the human cancer cell line HeLa, HepG-2, MCF-7, A549, K562 and TE-1. Reference: Phytochemistry. 2021 Jan;181:112542. https://pubmed.ncbi.nlm.nih.gov/33130373/
In vivo activity:
Samples of commercial partially purified saponin extract, quillaic acid, methyl 3β,16α-dihydroxy-23-oxoolean-12-en-28-oat and methyl 4-nor-3,16-dioxoolean-12-en-28-oate were assessed in mice using the topical tail-flick and i.p. hot-plate tests, respectively. The results of this study demonstrated that Quillaja saponaria saponins, quillaic acid, its methyl ester, and one of the oxidized derivatives of the latter, elicit dose-dependent antinociceptive effects in two murine thermal models. Reference: J Pharm Pharmacol. 2011 May;63(5):718-24. https://pubmed.ncbi.nlm.nih.gov/20951193/
Solvent mg/mL mM
Solubility
DMSO 41.0 84.24
Ethanol 14.0 28.77
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 486.69 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. Reichert CL, Salminen H, Weiss J. Quillaja Saponin Characteristics and Functional Properties. Annu Rev Food Sci Technol. 2019 Mar 25;10:43-73. doi: 10.1146/annurev-food-032818-122010. Epub 2019 Jan 21. PMID: 30664381. 2. Li F, Wu ST, Qu MH, Wang YX, Ma CL, Yu BH, Wang GS. Triterpenoid saponins from the herb Hylomecon japonica. Phytochemistry. 2021 Jan;181:112542. doi: 10.1016/j.phytochem.2020.112542. Epub 2020 Oct 22. PMID: 33130373. 3. Arrau S, Delporte C, Cartagena C, Rodríguez-Díaz M, González P, Silva X, Cassels BK, Miranda HF. Antinociceptive activity of Quillaja saponaria Mol. saponin extract, quillaic acid and derivatives in mice. J Ethnopharmacol. 2011 Jan 7;133(1):164-7. doi: 10.1016/j.jep.2010.09.016. Epub 2010 Oct 14. PMID: 20951193. 4. Rodríguez-Díaz M, Delporte C, Cartagena C, Cassels BK, González P, Silva X, León F, Wessjohann LA. Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. J Pharm Pharmacol. 2011 May;63(5):718-24. doi: 10.1111/j.2042-7158.2011.01263.x. Epub 2011 Apr 1. PMID: 21492174.
In vitro protocol:
1. Reichert CL, Salminen H, Weiss J. Quillaja Saponin Characteristics and Functional Properties. Annu Rev Food Sci Technol. 2019 Mar 25;10:43-73. doi: 10.1146/annurev-food-032818-122010. Epub 2019 Jan 21. PMID: 30664381. 2. Li F, Wu ST, Qu MH, Wang YX, Ma CL, Yu BH, Wang GS. Triterpenoid saponins from the herb Hylomecon japonica. Phytochemistry. 2021 Jan;181:112542. doi: 10.1016/j.phytochem.2020.112542. Epub 2020 Oct 22. PMID: 33130373.
In vivo protocol:
1. Arrau S, Delporte C, Cartagena C, Rodríguez-Díaz M, González P, Silva X, Cassels BK, Miranda HF. Antinociceptive activity of Quillaja saponaria Mol. saponin extract, quillaic acid and derivatives in mice. J Ethnopharmacol. 2011 Jan 7;133(1):164-7. doi: 10.1016/j.jep.2010.09.016. Epub 2010 Oct 14. PMID: 20951193. 2. Rodríguez-Díaz M, Delporte C, Cartagena C, Cassels BK, González P, Silva X, León F, Wessjohann LA. Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. J Pharm Pharmacol. 2011 May;63(5):718-24. doi: 10.1111/j.2042-7158.2011.01263.x. Epub 2011 Apr 1. PMID: 21492174.
1: Wang YC, Chen CR, Chen CY, Liang PH. Synthesis of Quillaic Acid through Sustainable C-H Bond Activations. J Org Chem. 2024 Apr 19;89(8):5491-5497. doi: 10.1021/acs.joc.3c02958. Epub 2024 Apr 10. PMID: 38595071; PMCID: PMC11040720. 2: Yang J, Liu Y, Zhong D, Xu L, Gao H, Keasling JD, Luo X, Chou HH. Combinatorial optimization and spatial remodeling of CYPs to control product profile. Metab Eng. 2023 Nov;80:119-129. doi: 10.1016/j.ymben.2023.09.004. Epub 2023 Sep 12. PMID: 37703999; PMCID: PMC10698227. 3: Li YH, Bai XS, Yang XX, Li YX, Li HR, Wang ZL, Wang W, Tian K, Huang XZ. Triterpenoid saponins from Psammosilene tunicoides and their antinociceptive activities. Phytochemistry. 2023 Oct;214:113795. doi: 10.1016/j.phytochem.2023.113795. Epub 2023 Jul 23. PMID: 37487918. 4: Raafat K, Al Haj M. Modulators of diabetic neuropathy and inflammation from Saponaria officinalis: Isolation of active phytochemicals and potential mechanisms of action. J Tradit Complement Med. 2023 Jan 5;13(3):226-235. doi: 10.1016/j.jtcme.2023.01.001. PMID: 37128196; PMCID: PMC10148123. 5: Marques MEM, de Carvalho AC, Yendo ACA, Magedans YVS, Zachert E, Fett-Neto AG. Phytotoxicity of Quillaja lancifolia Leaf Saponins and Their Bioherbicide Potential. Plants (Basel). 2023 Feb 2;12(3):663. doi: 10.3390/plants12030663. PMID: 36771747; PMCID: PMC9919483. 6: Makhmudova MM, Bacher M, Zengin G, Rosenau T, Youssef FS, Almasri DM, Elhady SS, Mamadalieva NZ. Silviridoside: A New Triterpene Glycoside from Silene viridiflora with Promising Antioxidant and Enzyme Inhibitory Potential. Molecules. 2022 Dec 11;27(24):8781. doi: 10.3390/molecules27248781. PMID: 36557914; PMCID: PMC9785594. 7: Huang X, Zhang CH, Deng H, Wu D, Guo HY, Lee JJ, Chen FE, Shen QK, Jin LL, Quan ZS. Synthesis and evaluation of anticancer activity of quillaic acid derivatives: A cell cycle arrest and apoptosis inducer through NF-κB and MAPK pathways. Front Chem. 2022 Sep 7;10:951713. doi: 10.3389/fchem.2022.951713. PMID: 36157038; PMCID: PMC9490060. 8: Yu GR, Lim DW, Karunarathne WAHM, Kim GY, Kim H, Kim JE, Park WH. A non-polar fraction of Saponaria officinalis L. acted as a TLR4/MD2 complex antagonist and inhibited TLR4/MyD88 signaling in vitro and in vivo. FASEB J. 2022 Jul;36(7):e22387. doi: 10.1096/fj.202200018RR. PMID: 35696068. 9: Wallace F, Fontana C, Ferreira F, Olivaro C. Structure Elucidation of Triterpenoid Saponins Found in an Immunoadjuvant Preparation of Quillaja brasiliensis Using Mass Spectrometry and 1H and 13C NMR Spectroscopy. Molecules. 2022 Apr 8;27(8):2402. doi: 10.3390/molecules27082402. PMID: 35458600; PMCID: PMC9024837. 10: Yazici Bektaş N, Ersoy E, Boğa M, Boran T, Çinar E, Özhan G, Gören AC, Eroğlu Özkan E. Cytotoxic and apoptotic effects of Hypericum androsaemum on prostate adenocarcinoma (PC-3) and hepatocellular carcinoma (Hep G2) cell lines with identification of secondary metabolites by LC-HRMS. Turk J Chem. 2021 Oct 19;45(5):1621-1638. doi: 10.3906/kim-2104-17. PMID: 34849072; PMCID: PMC8596555. 11: Li F, Wu ST, Qu MH, Wang YX, Ma CL, Yu BH, Wang GS. Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities. Carbohydr Res. 2021 Sep;507:108391. doi: 10.1016/j.carres.2021.108391. Epub 2021 Jul 7. PMID: 34271480. 12: Li F, Wu ST, Qu MH, Wang YX, Ma CL, Yu BH, Wang GS. Bioactive oleanane-type saponins from Hylomecon Japonica. Phytochemistry. 2021 Oct;190:112870. doi: 10.1016/j.phytochem.2021.112870. Epub 2021 Jul 14. PMID: 34271297. 13: Li W, Ma X, Li G, Zhang A, Wang D, Fan F, Ma X, Zhang X, Dai Z, Qian Z. De Novo Biosynthesis of the Oleanane-Type Triterpenoids of Tunicosaponins in Yeast. ACS Synth Biol. 2021 Aug 20;10(8):1874-1881. doi: 10.1021/acssynbio.1c00065. Epub 2021 Jul 14. PMID: 34259519. 14: Qiu H, Su L, Wang H, Zhang Z. Chitosan elicitation of saponin accumulation in Psammosilene tunicoides hairy roots by modulating antioxidant activity, nitric oxide production and differential gene expression. Plant Physiol Biochem. 2021 Sep;166:115-127. doi: 10.1016/j.plaphy.2021.05.033. Epub 2021 May 27. PMID: 34098155. 15: Hammami A, Farman M, Semmar N. Highlighting Aglycone-dependent Glycosylation Aspects in Caryophyllaceae Saponins by a Simplex Simulation Approach. Curr Top Med Chem. 2021;21(7):612-627. doi: 10.2174/1568026621666210114153216. PMID: 33459236. 16: Singh S, Florez H. Bioinformatic study to discover natural molecules with activity against COVID-19. F1000Res. 2020 Oct 6;9:1203. doi: 10.12688/f1000research.26731.1. PMID: 33145015; PMCID: PMC7590895. 17: Li F, Wu ST, Qu MH, Wang YX, Ma CL, Yu BH, Wang GS. Triterpenoid saponins from the herb Hylomecon japonica. Phytochemistry. 2021 Jan;181:112542. doi: 10.1016/j.phytochem.2020.112542. Epub 2020 Oct 22. PMID: 33130373. 18: Clochard J, Jerz G, Schmieder P, Mitdank H, Tröger M, Sama S, Weng A. A new acetylated triterpene saponin from Agrostemma githago L. modulates gene delivery efficiently and shows a high cellular tolerance. Int J Pharm. 2020 Nov 15;589:119822. doi: 10.1016/j.ijpharm.2020.119822. Epub 2020 Aug 27. PMID: 32861772. 19: Yu JS, Sahar NE, Bi YR, Jung K, Pang C, Huh JY, Kim KH. The Effects of Triterpenoid Saponins from the Seeds of Momordica cochinchinensis on Adipocyte Differentiation and Mature Adipocyte Inflammation. Plants (Basel). 2020 Aug 3;9(8):984. doi: 10.3390/plants9080984. PMID: 32756459; PMCID: PMC7466054. 20: Guzmán L, Villalón K, Marchant MJ, Tarnok ME, Cárdenas P, Aquea G, Acevedo W, Padilla L, Bernal G, Molinari A, Corvalán A. In vitro evaluation and molecular docking of QS-21 and quillaic acid from Quillaja saponaria Molina as gastric cancer agents. Sci Rep. 2020 Jun 29;10(1):10534. doi: 10.1038/s41598-020-67442-3. PMID: 32601436; PMCID: PMC7324585.