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Merck
CN

77536

Poncirin

analytical standard

Synonym(s):

(S)-5,7-Dihydroxy-4′-methoxyflavanone-7-[2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside], 4′-O-Methylnaringin, Isosakuranetin-7-neohesperidoside

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About This Item

Empirical Formula (Hill Notation):
C28H34O14
CAS Number:
14941-08-3
Molecular Weight:
594.56
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
329767754
EC Number:
239-020-1
Beilstein/REAXYS Number:
74301
MDL number:
MFCD00017476

Key Documents

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InChI key

NLAWPKPYBMEWIR-SKYQDXIQSA-N

InChI

1S/C28H34O14/c1-11-21(32)23(34)25(36)27(38-11)42-26-24(35)22(33)19(10-29)41-28(26)39-14-7-15(30)20-16(31)9-17(40-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-30,32-36H,9-10H2,1-2H3/t11-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1

SMILES string

COc1ccc(cc1)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)cc3O2

grade

analytical standard

assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

impurities

≤10.0% water

application(s)

food and beverages

format

neat

Quality Level

100

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General description

Poncirin is a flavanone glycoside, which is isolated from the water extract of fruits of Poncirus trifoliata. It is known to exhibit pharmacological properties such as anti-bacterial 
and anti-inflammatory activity.

Application

Poncirin (with other flavonoids of the bitter orange) was tested as a control agent for mosquito infestation, and was found to be larvacidal, to repel females from egg-laying on treated water, and to repel insects from biting topically treated human volunteers.
Poncirin may be used as a reference standard for the determination of poncirin in orange fruit extract using high-performance liquid chromatography coupled with diode array detector (HPLC-DAD).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ5118
BCCF6363
BCCF3394
BCCD7085
BCCC0857

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Inhibition of LPS-induced iNOS, COX-2 and cytokines expression by poncirin through the NF-kappaB inactivation in RAW 264.7 macrophage cells.
Kim B-J, et al.
Biological & Pharmaceutical Bulletin, 30(12), 2345-2351 (2007)
Poncirin promotes osteoblast differentiation but inhibits adipocyte differentiation in mesenchymal stem cells.
Yoon Y-H, et al.
European Journal of Pharmacology, 664(1-3), 54-59 (2011)
Determination of flavanones in orange juices obtained from different sources by HPLC/DAD.
Silva CRCL, et al.
Journal of Analytical Methods in Chemistry, 2014(1-3), 54-59 (2014)
Anti-Helicobacter pylori activity of the metabolites of poncirin from Poncirus trifoliata by human intestinal bacteria.
Kim B-J, et al.
Biological & Pharmaceutical Bulletin, 22(4), 422-424 (1999)

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