AZN-12499 | CAS#31712-49-9 | Flavanone glucoside

MedKoo Cat#: 465280 | Name: AZN-12499

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Description:

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

AZN-12499 is a flavanone glucoside that has been found in immature citrus fruits and has diverse biological activities. It active against H. pylori when used at a concentration of 0.5 mM. AZN-12499 scavenges DPPH radicals (IC50 = 2.04 mM) and inhibits the activity of intestinal maltase and HMG-CoA reductase (Kis = 1,800 and 9.8 µM, respectively, for the human enzymes) in cell-free assays. Dietary administration of AZN-12499 (2.5 and 5 g/kg diet) prevents decreases in bone mineral density in the femur of ovariectomized rats. This product has no formal name. For the convenience of scientific communication, we named it by combining its InChi Key (3 letters from the first letter of each section) with the last 5 digit of its CAS#) according to MedKoo Chemical Nomenclature (https://www.medkoo.com/page/naming).

Chemical Structure

AZN-12499

CAS#31712-49-9

Theoretical Analysis

MedKoo Cat#: 465280

Name: AZN-12499

CAS#: 31712-49-9

Chemical Formula: C22H24O11

Exact Mass: 464.1319

Molecular Weight: 464.42

Elemental Analysis: C, 56.90; H, 5.21; O, 37.89

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks
10mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

AZN-12499; AZN12499; AZN 12499; Hesperetin 7-O-glucoside;

IUPAC/Chemical Name

(S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one

InChi Key

ADSYMQORONDIDD-ZJHVPRRPSA-N

InChi Code

InChI=1S/C22H24O11/c1-30-14-3-2-9(4-11(14)24)15-7-13(26)18-12(25)5-10(6-16(18)32-15)31-22-21(29)20(28)19(27)17(8-23)33-22/h2-6,15,17,19-25,27-29H,7-8H2,1H3/t15-,17+,19+,20-,21+,22+/m0/s1

SMILES Code

OC1=C2C(O[C@H](C3=CC(O)=C(OC)C=C3)CC2=O)=CC(O[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O)CO)=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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

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	Solvent	mg/mL	mM
Solubility
	DMF	5.0	10.77
	DMSO	10.0	21.53
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.71

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 464.42 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

1: Wu F, Shi Z, Lei H, Chen G, Yuan P, Cao Z, Chen C, Zhu X, Liu C, Dong M, Song Y, Guo Y, Zhou J, Lu Y, Zhang L. Short-Term Intake of Hesperetin-7-O-Glucoside Affects Fecal Microbiota and Host Metabolic Homeostasis in Mice. J Agric Food Chem. 2021 Feb 10;69(5):1478-1486. doi: 10.1021/acs.jafc.0c05921. Epub 2020 Dec 22. PMID: 33351610. 2: Wan W, Xia N, Zhu S, Liu Q, Gao Y. A Novel and High-Effective Biosynthesis Pathway of Hesperetin-7-O-Glucoside Based on the Construction of Immobilized Rhamnosidase Reaction Platform. Front Bioeng Biotechnol. 2020 Jun 10;8:608. doi: 10.3389/fbioe.2020.00608. PMID: 32656196; PMCID: PMC7325963. 3: Kim DS, Lim SB. Semi-Continuous Subcritical Water Extraction of Flavonoids from Citrus unshiu Peel: Their Antioxidant and Enzyme Inhibitory Activities. Antioxidants (Basel). 2020 Apr 25;9(5):360. doi: 10.3390/antiox9050360. PMID: 32344942; PMCID: PMC7278842. 4: Liu X, Lin C, Ma X, Tan Y, Wang J, Zeng M. Functional Characterization of a Flavonoid Glycosyltransferase in Sweet Orange (Citrus sinensis). Front Plant Sci. 2018 Feb 15;9:166. doi: 10.3389/fpls.2018.00166. PMID: 29497429; PMCID: PMC5818429. 5: Escudero-López B, Cerrillo I, Gil-Izquierdo Á, Hornero-Méndez D, Herrero- Martín G, Berná G, Medina S, Ferreres F, Martín F, Fernández-Pachón MS. Effect of thermal processing on the profile of bioactive compounds and antioxidant capacity of fermented orange juice. Int J Food Sci Nutr. 2016 Nov;67(7):779-88. doi: 10.1080/09637486.2016.1204428. Epub 2016 Jul 7. PMID: 27385558. 6: Cheung TK, Li W, Ho HM, Liang ZT, Huang CQ. [Chemical variation in Aurantii Fructus before and after processing based on UHPLC-Q-TOF-MS]. Zhongguo Zhong Yao Za Zhi. 2016 Jun;41(11):2070-2080. Chinese. doi: 10.4268/cjcmm20161116. PMID: 28901103. 7: Fialovaa S, Veizerova L, Nosalova V, Drabikova K, Tekelova D, Grancai D, Sotnikova R. Water Extract of Mentha x villosa: Phenolic Fingerprint and Effect on Ischemia-Reperfusion Injury. Nat Prod Commun. 2015 Jun;10(6):937-40. PMID: 26197521. 8: Actis-Goretta L, Dew TP, Lévèques A, Pereira-Caro G, Rein M, Teml A, Schäfer C, Hofmann U, Schwab M, Eichelbaum M, Crozier A, Williamson G. Gastrointestinal absorption and metabolism of hesperetin-7-O-rutinoside and hesperetin-7-O-glucoside in healthy humans. Mol Nutr Food Res. 2015 Sep;59(9):1651-62. doi: 10.1002/mnfr.201500202. Epub 2015 Jun 23. PMID: 26018925. 9: Escudero-López B, Cerrillo I, Herrero-Martín G, Hornero-Méndez D, Gil- Izquierdo A, Medina S, Ferreres F, Berná G, Martín F, Fernández-Pachón MS. Fermented orange juice: source of higher carotenoid and flavanone contents. J Agric Food Chem. 2013 Sep 18;61(37):8773-82. doi: 10.1021/jf401240p. Epub 2013 Sep 4. PMID: 24004007. 10: Furtado AF, Nunes MA, Ribeiro MH. Hesperidinase encapsulation towards hesperitin production targeting improved bioavailability. J Mol Recognit. 2012 Nov;25(11):595-603. doi: 10.1002/jmr.2224. PMID: 23108619. 11: Lee YS, Huh JY, Nam SH, Moon SK, Lee SB. Enzymatic bioconversion of citrus hesperidin by Aspergillus sojae naringinase: enhanced solubility of hesperetin-7-O-glucoside with in vitro inhibition of human intestinal maltase, HMG-CoA reductase, and growth of Helicobacter pylori. Food Chem. 2012 Dec 15;135(4):2253-9. doi: 10.1016/j.foodchem.2012.07.007. Epub 2012 Jul 14. PMID: 22980799. 12: Lévèques A, Actis-Goretta L, Rein MJ, Williamson G, Dionisi F, Giuffrida F. UPLC-MS/MS quantification of total hesperetin and hesperetin enantiomers in biological matrices. J Pharm Biomed Anal. 2012 Jan 5;57:1-6. doi: 10.1016/j.jpba.2011.08.031. Epub 2011 Aug 26. PMID: 21920690. 13: Shimoda K, Hamada H. Production of hesperetin glycosides by Xanthomonas campestris and cyclodextrin glucanotransferase and their anti-allergic activities. Nutrients. 2010 Feb;2(2):171-80. doi: 10.3390/nu2020171. Epub 2010 Feb 9. PMID: 22254014; PMCID: PMC3257635. 14: Bredsdorff L, Nielsen IL, Rasmussen SE, Cornett C, Barron D, Bouisset F, Offord E, Williamson G. Absorption, conjugation and excretion of the flavanones, naringenin and hesperetin from alpha-rhamnosidase-treated orange juice in human subjects. Br J Nutr. 2010 Jun;103(11):1602-9. doi: 10.1017/S0007114509993679. Epub 2010 Jan 26. PMID: 20100371. 15: Gil-Izquierdo A, Riquelme MT, Porras I, Ferreres F. Effect of the rootstock and interstock grafted in lemon tree (Citrus limon (L.) Burm.) on the flavonoid content of lemon juice. J Agric Food Chem. 2004 Jan 28;52(2):324-31. doi: 10.1021/jf0304775. PMID: 14733516. 16: Bar-Peled M, Lewinsohn E, Fluhr R, Gressel J. UDP- rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus. J Biol Chem. 1991 Nov 5;266(31):20953-9. PMID: 1939145. 17: Choi JS, Yokozawa T, Oura H. Antihyperlipidemic effect of flavonoids from Prunus davidiana. J Nat Prod. 1991 Jan-Feb;54(1):218-24. doi: 10.1021/np50073a022. PMID: 2045817.

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