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24959-81-7 molecular structure
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(2E)-3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

ChemBase ID: 163531
Molecular Formular: C15H18O9
Molecular Mass: 342.29802
Monoisotopic Mass: 342.09508216
SMILES and InChIs

SMILES:
[C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)Oc1c(ccc(c1)/C=C/C(=O)O)O)O)O)O
Canonical SMILES:
OC[C@@H]1O[C@@H](Oc2cc(/C=C/C(=O)O)ccc2O)[C@H]([C@H]([C@@H]1O)O)O
InChI:
InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-5-7(1-3-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1
InChIKey:
QOPSZFXPZWQLOG-VHCZEJTMSA-N

Cite this record

CBID:163531 http://www.chembase.cn/molecule-163531.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2E)-3-(4-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
IUPAC Traditional name
caffeic acid 3-glucoside
Synonyms
3-[3-(β-D-Glucopyranosyloxy)-4-hydroxyphenyl]-2-propenoic Acid
3-(β-D-Glucopyranosyloxy)-4-hydroxy-cinnamic Acid
3-(β-D-Glucopyranosyloxy)-4-hydroxycinnamic Acid
Caffeic Acid 3-β-D-Glucoside
CAS Number
24959-81-7
PubChem SID
162257666
PubChem CID
5281759

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC C080025 external link Add to cart
PubChem 5281759 external link
Data Source Data ID Price
TRC
C080025 external link Add to cart Please log in.
Data Source Data ID
PubChem 5281759 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.425659  H Acceptors
H Donor LogD (pH = 5.5) -2.8021502 
LogD (pH = 7.4) -4.1370096  Log P -0.7391125 
Molar Refractivity 79.1661 cm3 Polarizability 31.22343 Å3
Polar Surface Area 156.91 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - C080025 external link
Found in the berries of wild potato species, believed to be an important biosynthetic intermediate. Studies have shown the ability of this compound to inhibit melanin formation when used as a component of topical skin creams.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Hanson, K., et al.: J. Biol. Chem., 238, 1105 (1963)
  • • Bernards, M., et al.: Phytochem., 30, 497 (1963)
  • • Lim, E., et al.: Biochem. J., 373, 987 (1963)
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PATENTS

PATENTS

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INTERNET

INTERNET

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