Naringin
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. — ChEBI
- IUPAC name
- (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
- Molecular formula
- C27H32O14
- Molecular weight
- 580.5 g/mol
- Exact mass
- 580.17920569 Da
- XLogP3
- -0.5
- Topological polar surface area
- 225.0 Ų
- Hydrogen-bond donors
- 8
- Hydrogen-bond acceptors
- 14
- Covalent units
- 1
- Defined stereocentres
- 11
Also known as
16 more reported names
External database identifiers
- ChEBI:CHEBI:28819
- ChEMBL:CHEMBL451532
- EPA DTXSID:DTXSID6022478
- PubMed:23108618
- PubMed:23107709
- PubMed:23000113
- PubMed:22986632
- PubMed:22985397
- PubMed:22965302
- PubMed:22958058
- PubMed:22957912
- PubMed:22953908
- PubMed:22953882
- PubMed:22953829
- PubMed:22940311
Evidence from additional scientific databases
EMBL-EBI ChEBI
naringin
A disaccharide derivative that is (S)-naringenin substituted by a 2-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
- Formula
- C27H32O14
- Average mass
- 580.539 g/mol
- Monoisotopic mass
- 580.17921 Da
- Formal charge
- 0
- (2S)-flavan-4-one — is a (CHEBI:140377)
- 4'-hydroxyflavanones — is a (CHEBI:140331)
- disaccharide derivative — is a (CHEBI:63353)
- dihydroxyflavanone — is a (CHEBI:38749)
- neohesperidoside — is a (CHEBI:25495)
- metabolite — has role (CHEBI:25212)
- antineoplastic agent — has role (CHEBI:35610)
- anti-inflammatory agent — has role (CHEBI:67079)
- (S)-naringenin — has functional parent (CHEBI:17846)
- metabolite — has role (CHEBI:25212)
- antineoplastic agent — has role (CHEBI:35610)
- anti-inflammatory agent — has role (CHEBI:67079)
- (2S)-flavan-4-one — is a (CHEBI:140377)
- 4'-hydroxyflavanones — is a (CHEBI:140331)
- disaccharide derivative — is a (CHEBI:63353)
- dihydroxyflavanone — is a (CHEBI:38749)
- neohesperidoside — is a (CHEBI:25495)
Additional curated names
Cross-references from this source
- REGISTRY_NUMBER: 102012 — Reaxys
- CAS: 10236-47-2 — KEGG COMPOUND
- CAS: 10236-47-2 — ChemIDplus
- MANUAL_X_REF: C00000983 — KNApSAcK
- MANUAL_X_REF: C09789 — KEGG COMPOUND
- MANUAL_X_REF: HMDB0002927 — HMDB
- MANUAL_X_REF: LSM-2038 — LINCS
- MANUAL_X_REF: Naringin — Wikipedia
- MANUAL_X_REF: NARINGIN — MetaCyc
Mapped by: Exact CAS cross-reference in the ChEBI compound record. Source updated: 2018-04-09. Retrieved: 2026-08-31. Open source record
NIH PubChem PUG-View
Attributed physical-property, hazard, environmental and use annotations.
- Boiling Point: 922.00 to 926.00 °C. @ 760.00 mm Hg Source: Human Metabolome Database (HMDB)
- LogP: -0.44 Source: Human Metabolome Database (HMDB)
- Melting Point: 83 °C Source: Human Metabolome Database (HMDB)
- Physical Description: Solid Source: Human Metabolome Database (HMDB)
- Solubility: 1 mg/mL at 40 °C Source: Human Metabolome Database (HMDB)
- Note: This chemical does not meet GHS hazard criteria for 76.1% (143 of 188) of all reports. Source: European Chemicals Agency (ECHA)
- Signal: Warning Source: European Chemicals Agency (ECHA)
- GHS Hazard Statements: H315 (23.9%): Causes skin irritation [Warning Skin corrosion/irritation]; H319 (23.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]; H335 (23.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] Source: European Chemicals Agency (ECHA)
- Precautionary Statement Codes: 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) Source: European Chemicals Agency (ECHA)
- ECHA C&L Notifications Summary: 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.; Reported as not meeting GHS hazard criteria per 143 of 188 reports by companies.; There are 6 notifications provided by 45 of 188 reports by companies with hazard statement code(s).; Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. Source: European Chemicals Agency (ECHA)
Mapped by: Existing checksum-valid CAS to unique PubChem CID match. Retrieved: 2026-08-31. Open source record
Scientific classifications and hazard annotations provide context and do not replace the market-specific regulatory decision shown above.
Additional source coverage and match status
| Source | Result | Checked |
|---|---|---|
| EMBL-EBI ChEBI | Exact match | 2026-08-31 |
| NIH PubChem PUG-View | Exact match | 2026-08-31 |
A recorded no-match is useful evidence that the source was checked; it is not a claim that the substance does not exist elsewhere.
Retrieved from NIH PubChem on 2026-08-31 by checksum-valid CAS matching. Chemical properties do not replace the regulatory decision on this page.