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Basic information
- CAS
10236-47-2- Standard SMILES
C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3cc(O)c4c(c3)O[C@H](c3ccc(O)cc3)CC4=O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O- InChIKey
DFPMSGMNTNDNHN-ZPHOTFPESA-N- Molecular formula
- C27H32O14
- Average molar mass
- 580.5 g/mol
- Monoisotopic mass
- 580.1792057
Overview
Naringin 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. It has a role as a metabolite, an antineoplastic agent and an anti-inflammatory agent. It is a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one, a neohesperidoside, a dihydroxyflavanone and a disaccharide derivative. It is functionally related to a (S)-naringenin.
Names & identifiers
- Preferred name
- Naringin
- IUPAC
- (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Names & synonyms
naringin10236-47-2aurantiinNaringosideNaringenin 7-O-neohesperidosideN7TD9J649BNaringenin-7-beta-neohesperidoside(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneDTXSID6022478CHEBI:28819(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon
Show more names
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]4',5,7-trihydroxyflavanone 7-rhamnoglucosideNaringenin 7-O-(alpha-L-rhamnosyl-(1->2)-beta-D-glucoside)Citrus naringinine(2S)-7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one(2S)-7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one(2S)-7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
Properties
Computed structural propertiesFilling in
- XLogP
- -0.5
- Topological polar surface area
- 225 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 41
- Formal charge
- 0
- Complexity
- 884
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
LogP
-0.44
-0.44
Flavoring AgentsEU Flavoring substances
Solubility1 mg/mL at 40 °C
Boiling Point922.00 to 926.00 °C. @ 760.00 mm Hg
Melting Point83 °C
Physical DescriptionSolid
Collision Cross Section
230.6 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
237.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
217.33 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
233.5 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
239.1 Ų [M+H]+
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 76.1% (143 of 188) of all reports.
Warning
H315 (23.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 188 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (S)-
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 11-10-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20764
Naringin: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and CategoriesSkin Irrit. 2 (23.9%)
Chemistry & industry
Pharmacology
Tissue LocationsEpidermis
Cellular LocationsCytoplasm
Uses & manufacturing
General Manufacturing Information4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-: ACTIVE
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
西安天朗源生物科技有限公司17749038280 17749038280 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Shaanxi Huike Botanical Development Co., Ltd+86-29-62663046 · [email protected]
Related reactions
3 records
Compound notes
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