ContaminantDB: HESPERIDIN

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-19 02:08:14 UTC

Update Date

2016-10-28 10:02:36 UTC

Accession Number

CHEM005941

Identification

Common Name

HESPERIDIN

Class

Small Molecule

Description

Hesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit. Hesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit due to vitamin C deficiency such as bruising due to capillary fragility were found in early studies to be relieved by crude vitamin C extract but not by purified vitamin C. The bioflavonoids, formerly called "vitamin P", were found to be the essential components in correcting this bruising tendency and improving the permeability and integrity of the capillary lining. These bioflavonoids include hesperidin, citrin, rutin, flavones, flavonols, catechin and quercetin. Of historical importance is the observation that "citrin", a mixture of two flavonoids, eriodictyol and hesperidin, was considered to possess a vitamin-like activity, as early as in 1949. Hesperidin deficiency has since been linked with abnormal capillary leakiness as well as pain in the extremities causing aches, weakness and night leg cramps. Supplemental hesperidin also helps in reducing oedema or excess swelling in the legs due to fluid accumulation. As with other bioflavonoids, hesperidin works best when administered concomitantly with vitamin C. No signs of toxicity have been observed with normal intake of hesperidin. Hesperidin was first discovered in 1827, by Lebreton, but not in a pure state and has been under continuous investigation since then (PMID: 11746857).

Contaminant Sources

Cosmetic Chemicals
EAFUS Chemicals
FooDB Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
7-Rhamnoglucoside, hesperetin	HMDB
Hesperetin 7-rhamnoglucoside	HMDB
Hesperetin-7-rutinoside	HMDB
Atripliside b	HMDB
Hesperetin 7 rhamnoglucoside	HMDB
Hesperetin 7 rutinoside	HMDB
(2S)-Hesperidin	HMDB
(S)-(-)-Hesperidin	HMDB
Cirantin	HMDB
Ciratin	HMDB
Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-a-L-rhamnosyl-D-glucoside) (7ci)	HMDB
Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-alpha-L-rhamnosyl-delta-glucoside) (7ci)	HMDB
Hesper bitabs	HMDB
Hesperetin 7-O-rutinoside	HMDB
Hesperetin-rutinoside	HMDB
Hesperidine	HMDB
Hesperidoside	HMDB
Hesperitin-7-rhamnoglucoside	HMDB
2S, Hesperidin	MeSH
Hesperidin 2S	MeSH
Hesperidin	MeSH

Chemical Formula

C₂₈H₃₄O₁₅

Average Molecular Mass

610.561 g/mol

Monoisotopic Mass

610.190 g/mol

CAS Registry Number

520-26-3

IUPAC Name

(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

hesperidine

SMILES

COC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O[C@@H]1O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]1O)C=C2O

InChI Identifier

InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1

InChI Key

QUQPHWDTPGMPEX-QJBIFVCTSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Vinylogous acid
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.69 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.31	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.61	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	140.77 m³·mol⁻¹	ChemAxon
Polarizability	59.87 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-7432290000-b2e363b3a4573c409d87	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-066r-7330019000-b63391bb7f1e41c9f778	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0udi-0009000000-283330c229581467aa8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0002009000-ef46dd12935025cc99f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0009002000-4750b2aa846256abc7dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0010009000-7d463589853787a4d83a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-0udi-0029000000-5abbbe61f9472ac9f446	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0udi-0009000000-865b6028ed5cc1fd73d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-2924000000-2288595ee1b67877de4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0000009000-8c42f8adffac7d78b94c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-0006009000-1f68460ef007fbd1cfa9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009002000-26d653ee690ce5c6cd20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009000000-a4d68b31e046fbf057d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0019000000-e9135e61d5aa11f40135	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0119003000-80c5f918f82d46fc1131	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udl-0449354000-fbc98e9137414ef7f9d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0798110000-16e3084699e73d1ab59d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udj-0922000000-3a62c905fced57caf060	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0r00-5649448000-9cac05e933663578912d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-3759130000-62395a3dbb85c7dd9d09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-3698000000-d4e4fc069a84c3e6d9e0	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum