Naringin

Naringin
Compound Structure:
Synonyms: (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; naringin; Naringoside; aurantiin; (2S)-Naringin
Compound ID: NMPC-1291
PubChem ID:

442428

Molecular Formula: C27H32O14
Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
InChIKey: DFPMSGMNTNDNHN-ZPHOTFPESA-N
About the compound:

Naringin is a flavanone-7-O-glycoside between the flavanonenaringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness created by naringin. In humans naringin is metabolized to the aglyconenaringenin (not bitter) by naringinase present in the gut.

GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

580.5 g/mol

XLogP3-AA

-0.5

Hydrogen Bond Donor Count

8

Hydrogen Bond Acceptor Count

14

Rotatable Bond Count

6

Exact Mass

580.17920569 g/mol

Monoisotopic Mass

580.17920569 g/mol

Topological Polar Surface Area

225Ų

Heavy Atom Count

41

Formal Charge

0

Complexity

884

Isotope Atom Count

0

Defined Atom Stereocenter Count

11

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Boiling Point

922.00 to 926.00 °C. @ 760.00 mm Hg

Source: PubChem            

Source Species: Senna alata
Talinum triangulare
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