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71162

Sigma-Aldrich

Naringin

≥95% (HPLC)

Synonym(s):

4′,5,7-Trihydroxyflavanone 7-rhamnoglucoside, Naringenin 7-neohesperidoside, Naringenine-7-rhamnosidoglucoside, Naringoside

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About This Item

Empirical Formula (Hill Notation):
C27H32O14
CAS Number:
10236-47-2
Molecular Weight:
580.53
Beilstein:
102012
EC Number:
233-566-4
MDL number:
MFCD00148888
UNSPSC Code:
12352201
PubChem Substance ID:
57652274
NACRES:
NA.47
Pricing and availability is not currently available.

Quality Level

200

Assay

≥95% (HPLC)

form

powder

optical activity

[α]20/D −80±10°, c = 1% in ethanol

mp

83  °C ((181 °F ))

solubility

ethanol: o.1 g/10 mL, clear to hazy, colorless to light greenish-yellow

SMILES string

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2Oc3cc(O)c4C(=O)CC(Oc4c3)c5ccc(O)cc5)[C@H](O)[C@H](O)[C@H]1O

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

InChI key

DFPMSGMNTNDNHN-JJLSSNRUSA-N

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Application

Naringin has been used:
  • as a bitter tastant to compare the behavioral response of the Drosophila larva and adult(2)
  • to study its anti-inflammatory property and to determine its effect on nucleus pulposus (NP) cells(3)
  • to determine its effect on bone metabolism like osteogenic differentiation, inhibition of osteoclast formation(4)

Biochem/physiol Actions

Naringin can interact with signaling molecules and modulates signaling pathways. It possesses anti-inflammatory and anti-cancer activities. It also exhibits pharmacological effects on oxidative stress, bone regeneration, genetic damage, metabolic syndrome and central nervous system (CNS) diseases.[1]
Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.

Other Notes

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8754
BCCJ7548
BCCG5679
BCCF4512
BCCC2187

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Marcelo Silva et al.
Industrial & engineering chemistry research, 57(28), 9210-9221 (2018-10-03)
Liquid-liquid extraction (LLE) can be an effective strategy for the purification of polyphenols from a fermentation broth. However, solvents need to be chosen to ensure high extraction capacity and selectivity. For that purpose, a systematic study is here presented, where
Therapeutic potential of naringin: an overview
Chen R, et al.
Pharmaceutical biology, 54(12), 3203-3210 (2016)
Luís F Mendes et al.
Scientific reports, 9(1), 14906-14906 (2019-10-19)
The ability of flavonoids to attenuate macrophage pro-inflammatory activity and to promote macrophage-mediated resolution of inflammation is still poorly understood at the biochemical level. In this study, we have employed NMR metabolomics to assess how therapeutically promising flavonoids (quercetin, naringenin
Jiukai Zhang et al.
Food chemistry, 135(3), 1471-1478 (2012-09-08)
Huyou (Citrus changshanensis) is rich in naringin and neohesperidin, which are natural flavanone glycosides with a range of biological activities. Among the different fruit parts, i.e. flavedo, albedo, segment membrane (SM), and juice sacs (JS), albedo showed the highest contents
Yi-Chu Nie et al.
Journal of medicinal food, 15(10), 894-900 (2012-09-19)
Naringin, a well-known flavanone glycoside of grapefruit and citrus fruits, was found to be as an effective anti-inflammatory compound in our previous lipopolysaccharide-induced acute lung injury mouse model via blockading activity of nuclear factor κB. The current study sought to
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Questions

1–4 of 4 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. What is the stereochemistry of this compound? Is it R or S ?

    1 answer

    1. This product is the S form of Naringin. The material is a disaccharide derivative that is (S)-naringenin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. The compound has a total of eleven chiral centers.

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  4. Is this product available?

    1 answer

    1. The availability of this product may differ from region to region or country to country. The information you are requesting can be supplied by our Technical Service team who can assist you with further. We kindly ask you to navigate to the link https://www.sigmaaldrich.com/techservice, click on "Product Technical Inquires" under the Products Section with all the required information so that a member of our team can reach out to you to assist further. Thank you.

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