Naringin
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MedKoo CAT#: 540311

CAS#: 10236-47-2

Description: Naringin is a SERM(selective estrogen receptor modulator) found in citrus fruits. It exhibits a wide variety of biological activities, including inhibiting the release of VEGF in ER+ breast cancer cells, improving colchicine-induced deficits in cognitive performance, attenuating oxidative damage, and suppressing gentamicin-induced pro-inflammatory cytokine expresion.


Price and Availability

Size Price Shipping out time Quantity
5g USD 195 2 Weeks
10g USD 320 2 Weeks
25g USD 415 2 Weeks
50g USD 650 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-08-11. Prices are subject to change without notice.

Naringin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540311
Name: Naringin
CAS#: 10236-47-2
Chemical Formula: C27H32O14
Exact Mass: 580.1792
Molecular Weight: 580.53
Elemental Analysis: C, 55.86; H, 5.56; O, 38.58


Synonym: Aurantiin; AI3-19008; AI319008; AI3 19008; Naringin; Naringoside

IUPAC/Chemical Name: 7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

InChi Key: DFPMSGMNTNDNHN-JJLSSNRUSA-N

InChi Code: InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16?,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

SMILES Code: O=C1CC(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O[C@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)O)O)O)=C3


Technical Data

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:
>2 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


References

1: Bharti S, Rani N, Krishnamurthy B, Arya DS. Preclinical evidence for the pharmacological actions of naringin: a review. Planta Med. 2014 Apr;80(6):437-51. doi: 10.1055/s-0034-1368351. Epub 2014 Apr 7. Review. PubMed PMID: 24710903.

2: Li NH, Xu ZW. [Naringin reduced polymethylmethacrylate-induced osteolysis in the mouse air sacs model]. Zhongguo Gu Shang. 2015 Apr;28(4):345-9. Chinese. PubMed PMID: 26072618.

3: Chen F, Zhang N, Ma X, Huang T, Shao Y, Wu C, Wang Q. Naringin Alleviates Diabetic Kidney Disease through Inhibiting Oxidative Stress and Inflammatory Reaction. PLoS One. 2015 Nov 30;10(11):e0143868. doi: 10.1371/journal.pone.0143868. eCollection 2015. PubMed PMID: 26619044; PubMed Central PMCID: PMC4664292.

4: Yin FM, Xiao LB, Zhang Y. [Research progress on Drynaria fortunei naringin on inflammation and bone activity]. Zhongguo Gu Shang. 2015 Feb;28(2):182-6. Review. Chinese. PubMed PMID: 25924506.

5: Kulasekaran G, Ganapasam S. Neuroprotective efficacy of naringin on 3-nitropropionic acid-induced mitochondrial dysfunction through the modulation of Nrf2 signaling pathway in PC12 cells. Mol Cell Biochem. 2015 Nov;409(1-2):199-211. doi: 10.1007/s11010-015-2525-9. Epub 2015 Aug 18. PubMed PMID: 26280522.

6: Takumi S, Ikema S, Hanyu T, Shima Y, Kurimoto T, Shiozaki K, Sugiyama Y, Park HD, Ando S, Furukawa T, Komatsu M. Naringin attenuates the cytotoxicity of hepatotoxin microcystin-LR by the curious mechanisms to OATP1B1- and OATP1B3-expressing cells. Environ Toxicol Pharmacol. 2015 Mar;39(2):974-81. doi: 10.1016/j.etap.2015.02.021. Epub 2015 Mar 7. PubMed PMID: 25818985.

7: Jiao HY, Su WW, Li PB, Liao Y, Zhou Q, Zhu N, He LL. Therapeutic effects of naringin in a guinea pig model of ovalbumin-induced cough-variant asthma. Pulm Pharmacol Ther. 2015 Aug;33:59-65. doi: 10.1016/j.pupt.2015.07.002. Epub 2015 Jul 10. PubMed PMID: 26169899.

8: Raha S, Yumnam S, Hong GE, Lee HJ, Saralamma VV, Park HS, Heo JD, Lee SJ, Kim EH, Kim JA, Kim GS. Naringin induces autophagy-mediated growth inhibition by downregulating the PI3K/Akt/mTOR cascade via activation of MAPK pathways in AGS cancer cells. Int J Oncol. 2015 Sep;47(3):1061-9. doi: 10.3892/ijo.2015.3095. Epub 2015 Jul 20. PubMed PMID: 26201693.

9: Ahmad SF, Attia SM, Bakheet SA, Zoheir KM, Ansari MA, Korashy HM, Abdel-Hamied HE, Ashour AE, Abd-Allah AR. Naringin attenuates the development of carrageenan-induced acute lung inflammation through inhibition of NF-κb, STAT3 and pro-inflammatory mediators and enhancement of IκBα and anti-inflammatory cytokines. Inflammation. 2015 Apr;38(2):846-57. doi: 10.1007/s10753-014-9994-y. PubMed PMID: 25117567.

10: Wang L, Zhang YG, Wang XM, Ma LF, Zhang YM. Naringin protects human adipose-derived mesenchymal stem cells against hydrogen peroxide-induced inhibition of osteogenic differentiation. Chem Biol Interact. 2015 Dec 5;242:255-61. doi: 10.1016/j.cbi.2015.10.010. Epub 2015 Oct 19. PubMed PMID: 26482937.

11: Qi Z, Xu Y, Liang Z, Li S, Wang J, Wei Y, Dong B. Naringin ameliorates cognitive deficits via oxidative stress, proinflammatory factors and the PPARγ signaling pathway in a type 2 diabetic rat model. Mol Med Rep. 2015 Nov;12(5):7093-101. doi: 10.3892/mmr.2015.4232. Epub 2015 Aug 20. PubMed PMID: 26300349.

12: Fan J, Li J, Fan Q. Naringin promotes differentiation of bone marrow stem cells into osteoblasts by upregulating the expression levels of microRNA-20a and downregulating the expression levels of PPARγ. Mol Med Rep. 2015 Sep;12(3):4759-65. doi: 10.3892/mmr.2015.3996. Epub 2015 Jun 24. PubMed PMID: 26126997.

13: Surampalli G, K Nanjwade B, Patil PA. Corroboration of naringin effects on the intestinal absorption and pharmacokinetic behavior of candesartan cilexetil solid dispersions using in-situ rat models. Drug Dev Ind Pharm. 2015;41(7):1057-65. doi: 10.3109/03639045.2014.925918. Epub 2014 Jun 11. PubMed PMID: 24918161.

14: Wang D, Ma W, Wang F, Dong J, Wang D, Sun B, Wang B. Stimulation of Wnt/β-Catenin Signaling to Improve Bone Development by Naringin via Interacting with AMPK and Akt. Cell Physiol Biochem. 2015;36(4):1563-76. doi: 10.1159/000430319. Epub 2015 Jul 10. PubMed PMID: 26159568.

15: Li CH, Wang JW, Ho MH, Shih JL, Hsiao SW, Thien DV. Immobilization of naringin onto chitosan substrates by using ozone activation. Colloids Surf B Biointerfaces. 2014 Mar 1;115:1-7. doi: 10.1016/j.colsurfb.2013.11.006. Epub 2013 Nov 15. PubMed PMID: 24317428.

16: Cao X, Lin W, Liang C, Zhang D, Yang F, Zhang Y, Zhang X, Feng J, Chen C. Naringin rescued the TNF-α-induced inhibition of osteogenesis of bone marrow-derived mesenchymal stem cells by depressing the activation of NF-кB signaling pathway. Immunol Res. 2015 Jul;62(3):357-67. doi: 10.1007/s12026-015-8665-x. PubMed PMID: 26032685.

17: Wang D, Yan J, Chen J, Wu W, Zhu X, Wang Y. Naringin Improves Neuronal Insulin Signaling, Brain Mitochondrial Function, and Cognitive Function in High-Fat Diet-Induced Obese Mice. Cell Mol Neurobiol. 2015 Oct;35(7):1061-71. doi: 10.1007/s10571-015-0201-y. Epub 2015 May 5. PubMed PMID: 25939427.

18: Li F, Sun X, Ma J, Ma X, Zhao B, Zhang Y, Tian P, Li Y, Han Z. Naringin prevents ovariectomy-induced osteoporosis and promotes osteoclasts apoptosis through the mitochondria-mediated apoptosis pathway. Biochem Biophys Res Commun. 2014 Sep 26;452(3):629-35. doi: 10.1016/j.bbrc.2014.08.117. Epub 2014 Aug 30. PubMed PMID: 25181344.

19: Adil M, Kandhare AD, Visnagri A, Bodhankar SL. Naringin ameliorates sodium arsenite-induced renal and hepatic toxicity in rats: decisive role of KIM-1, Caspase-3, TGF-β, and TNF-α. Ren Fail. 2015;37(8):1396-407. doi: 10.3109/0886022X.2015.1074462. Epub 2015 Sep 3. PubMed PMID: 26337322.

20: Li N, Xu Z, Wooley PH, Zhang J, Yang SY. Therapeutic potentials of naringin on polymethylmethacrylate induced osteoclastogenesis and osteolysis, in vitro and in vivo assessments. Drug Des Devel Ther. 2013 Dec 10;8:1-11. doi: 10.2147/DDDT.S52714. eCollection 2014. PubMed PMID: 24376342; PubMed Central PMCID: PMC3864877.