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13463-28-0 molecular structure
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(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

ChemBase ID: 155911
Molecular Formular: C27H32O15
Molecular Mass: 596.53398
Monoisotopic Mass: 596.17412032
SMILES and InChIs

SMILES:
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)O[C@@H](CC2=O)c1ccc(c(c1)O)O)O)O)O)O)O)O)O
Canonical SMILES:
O[C@@H]1[C@@H](O)[C@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(c(c2)O)O)O[C@@H]([C@H]1O)CO[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI:
InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
InChIKey:
OMQADRGFMLGFJF-MNPJBKLOSA-N

Cite this record

CBID:155911 http://www.chembase.cn/molecule-155911.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
IUPAC Traditional name
eriocitrin
Synonyms
(S)-3′,4′,5,7-Tetrahydroxyflavanone-7-[6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside]
Eriocitrin
CAS Number
13463-28-0
EC Number
236-668-7
MDL Number
MFCD00017472
Beilstein Number
1304401
PubChem SID
24869120
162250049
PubChem CID
83489

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 83489 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.119624  H Acceptors 15 
H Donor LogD (pH = 5.5) -0.4605546 
LogD (pH = 7.4) -0.46862283  Log P -0.46045104 
Molar Refractivity 136.2847 cm3 Polarizability 54.79462 Å3
Polar Surface Area 245.29 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
Grade
analytical standard expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C27H32O15 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 45714 external link
Biochem/physiol Actions
Flavone glycoside found in lemon. Administration prior to acute exercise helped to maintain the redox status of liver glutathione. Without eriocitrin, it shifts markedly toward oxidized form.1
Sigma Aldrich - 94113 external link
Biochem/physiol Actions
Flavone glycoside found in lemon. Administration prior to acute exercise helped to maintain the redox status of liver glutathione. Without eriocitrin, it shifts markedly toward oxidized form.1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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