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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)-, (2S)-

HCID 4441
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
10236-47-2
Standard SMILES
CC1OC(OC2C(Oc3cc(O)c4c(c3)OC(c3ccc(O)cc3)CC4=O)OC(CO)C(O)C2O)C(O)C(O)C1O
InChIKey
DFPMSGMNTNDNHN-UHFFFAOYSA-N
Molecular formula
C27H32O14
Average molar mass
580.5 g/mol
Monoisotopic mass
580.17920569

Overview

naringine has been reported in Punica granatum with data available.

Names & identifiers

Preferred name
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)-, (2S)-
IUPAC
7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
English name
Naringin
Molecular formula
C27H32O14
Molecular weight
580.54

Names & synonyms

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)-, (2S)-7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one4H-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)-7-(4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneRefChem:5273344H-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)-Naringenin 7-Rhamnoglucoside7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one58001-41-54H-1-Benzopyran-4-one,7-[[2-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2R)-NSC93745Naringin (4',5,7-trihydroxyflavanone 7-rhamnoglucoside)
Show more names
FEMA 2769NARINGENIN-7-O-NEOHESPERIDOSIDENaringCabinda bark extractnaringoside(2S)-NaringinNARINGIN WITH HPLCCitrus grandis OsbeckNARINGENIN-7-RHAMNOGLUCOSIDE7-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
ISOHESPERIDIN, PRACTNaringenin 7-neohesperidosideSCHEMBL13237107DTXSID10860071DFPMSGMNTNDNHN-UHFFFAOYSA-NHMS3369C10HMS3374A04HMS3651C20

Database identifiers

CAS
10236-47-2
PubChem CID
4441
DTXSID
DTXSID10860071

Properties

Computed structural properties

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

Physicochemical properties

Melting point
166 °C · 166 °C
alpha
-91 · -91 º (c=1, C2H5OH)
Boiling point
559.35 °C · 559.35°C (rough estimate)
Density
1.3285 · 1.3285 (rough estimate)
vapor pressure
2.25 Pa · 2.25Pa at 20℃
refractive index
-84 ° · -84 ° (C=2, EtOH)
FEMA
2769 · 2769 | NARINGEN EXTRACT (CITRUS PARADISI MACF.)
FLAVIS Number
16.058 · 16.058 | Naringin
storage temp.
2 · 2-8°C
solubility
1 mg/mL · DMSO : 1 mg/mL (1.72 mM; Need ultrasonic)H2O : 1 mg/mL (1.72 mM; ultrasonic and warming and heat to 80°C)
form
crystalline
pka
7.17 · 7.17±0.40(Predicted)
color
off-white
biological source
citrus fruit
optical activity
20 · [α]20/D 80±10°, c = 1% in ethanol
Water Solubility
Soluble in water, alcohol, acetone and warm acetic acid.
Merck
14 · 14,6425
BRN
102012 · 102012
Major Application
cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
Cosmetics Ingredients Functions
SKIN PROTECTING
InChIKey
DFPMSGMNTNDNHN-JJLSSNRUSA-N
SMILES
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
LogP
-0.44 at · -0.44 at 20℃
CAS DataBase Reference
10236 · 10236-47-2(CAS DataBase Reference)
FDA 21 CFR
182.2 · 182.20; 582.20
EWG's Food Scores
1 · 1
FDA UNII
7 TD9J649B · N7TD9J649B
EPA Substance Registry System
4 H-1-Benzopyran-4-one, · 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)-, (2S)- (10236-47-2)
UNSPSC Code
85151701 · 85151701
NACRES
47 · NA.47
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
301 · P301+P312+P330
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/37/38
Safety Statements
22 · 22-24/25-36-26
WGK Germany
3 · 3
RTECS
6340000 · QN6340000
F
3 · 3
TSCA
TSCA listed
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
REACH Registrations
Active

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory InformationNaringin: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
3
wgk
3
tsca
TSCA listed
rtecs
QN6340000
hs_code
29389090
risk_code
22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
safety_code
22-24/25-36-26
Storage Class
11 - Combustible Solids
Hazard statements
H302
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P301+P312+P330

Chemistry & industry

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
Applications · 6 items

DescriptionNaringin is also called naringoside, hesperidin, and isohesperidin. It is a pale yellow flavanone compound extracted from immature or nearly mature outer layer of C. paradisi Macfad which belongs to Citrus grandis (L.) Osbeck. In terms of traditional Chinese medicine, the flavor of grapefruit is sweet and sour, and the nature is cold; the flavors of its peel are sweet, pungent, and bitter, and the nature of its peel is warm. Both the pulp and the peel of grapefruit have the bio logical function including reducing phlegm, helping digestion, relieving abdominal distention, and fast diaphragm. And they are mainly used for the treatment of cough with asthma, sense of suppression in the chest, coldness and pain in abdomen, dys peptic retention, and hernia.

HistoryNaringin is mainly existed in the peel of grapefruit, lime, and their varieties; it has multiple biological activities and is widely applied in the fields of medicine, food, and cosmetics. In the 1930s, Harvey and Rygg obtained naringin through the method of isolation and extraction. They also established a colorimetric method for the determination of naringin, which laid the foundation for the following researches . Booth and other researchers conducted the systematic researches on the narin gin metabolites . In the 1960s, Hagen and other researchers established a fluores cence chromatography method for the determination naringin . In addition, the biological activity of naringin was evaluated. It was observed to improve ascites, experimental pulmonary edema, peritonitis, and oxygenation . At present, the extraction methods of naringin are hot water extraction, alkali extraction, and acid precipitation and organic solvent extraction. A series of pharmacological activity studies have been conducted and demonstrated its various biological activities .

UsesNaringin 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)

UsesNaringoside is a metabolite of Naringin (N378980), a major flavonoid found in grapefruit juice. It has antioxidant, lipid lowering, and anticancer activities. It is also an inhibitor of cytochrome P450 enzymes, affecting drug metabolism and thus drug absorption in humans.

Usesantihaemorrhagic, antiinflammatory

General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Upstream & downstream products

Downstream products

beta-PhenylpropiophenoneNeosperidin dihydrochalconeRHOIFOLINIsosakuraninNaringin dihydrochalconeAPIGENINTRIACETATE

Suppliers101 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]
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]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
南京丙承生物科技有限公司18805194892 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]

Additional notes

DefinitionChEBI: A disaccharide derivative that is (S)-naringenin substituted by a 2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosi ic linkage.

Related reactions

1 records
New reaction record
HRID 116627 reaction equation
HRID 116627As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
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上海隆盛化工有限公司58099637 13585536065 · [email protected]
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杭州东帆化学有限公司86-0571-85151182
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四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
成都健腾生物技术有限公司86-28-85159085 · [email protected]
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上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
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AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
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上海贤鼎生物科技有限公司4009209199 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
陕西帕尼尔生物科技有限公司13720616393;029-84385017-8003 13720616393 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]