Products for Research Use Only
RegisterLogin

5-O-Caffeoylshikimic acid

CAT: 0931-TN1295-01Size: 1 mgDry Ice: NoHazardous: No
Product image 1
1 / 1
CAT#:0931-TN1295-01Size:1 mg
Selected
24/48H Stock Items & 2 to 6 Weeks non Stock Items.
Quick Request Actions
CAS Number
73263-62-4
Target
IL Receptor, TNF, NO Synthase
Related Pathways
Immunology/Inflammation, Apoptosis
Purity
0.9982
Bioactivity
5-O-Caffeoylshikimic acid shows anti-oxidative activity; it also shows anti-inflammatory activity, the underlying mechanism was associated with downregulation of nuclear factor-κB.
Smiles
O[C@@H]1C=C(C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@@H]1O)C(O)=O
Molecular Formula
C16H16O8
Molecular Weight
336.29
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

5-O-Caffeoylshikimic acid

5-[(E)-caffeoyl]shikimic acid is a carboxylic ester obtained by formal condensation of the carboxy group of (E)-caffeic acid with the 5-hydroxy group of shikimic acid. It has a role as a plant metabolite. It is a cyclohexenecarboxylic acid, a carboxylic ester, a member of catechols and an alpha,beta-unsaturated monocarboxylic acid. It is functionally related to a shikimic acid and a trans-caffeic acid. It is a conjugate acid of a 5-[(E)-caffeoyl]shikimate.

CAS Number73263-62-4
PubChem CID5281762
IUPAC Name(3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
Molecular FormulaC16H16O8
Molecular Weight336.29
XLogP0.2
Topological Polar Surface Area145
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Heavy Atom Count24
Formal Charge0
Complexity540
SMILES
C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O
InChI
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1
InChIKey
QMPHZIPNNJOWQI-GDDAOPKQSA-N
Chemical Structure
2D Structure
2D structure of 5-O-Caffeoylshikimic acid
CAS: 73263-62-4
CID: 5281762
Formula: C16H16O8
MW: 336.29
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight336.29
XLogP30.2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass336.08451746
Monoisotopic Mass336.08451746
Topological Polar Surface Area145 Ų
Heavy Atom Count24
Formal Charge0
Complexity540
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Related Products

CatalogName
T125535-013-O-Caffeoylshikimic acid
TN3052-014-O-Caffeoylshikimic acid
TN7473-015-O-Coumaroylquinic acid
TN3131-015-O-Cinnamoylquinic acid
T39107-015-O- (3'-O-Glucosylcaffeoyl) quinic acid
T83330-014,5-Di-O-caffeoylquinic acid
T123852-013,5-Di-O-galloylshikimic acid
T124062-013,5-Di-O-galloylquinic acid
T124940-013,8-Di-O-methylellagic acid 2-O-(5'-O-acetyl)arabinofuranoside
TYD-00686-015,6-O-Isopropylidene-L-ascorbic acid

Alternative Products

CatalogName
GTR19155006-015-O-Caffeoylshikimic acid
HY-N8321R5-O-Caffeoylshikimic acid (Standard)
HY-N86504-O-Caffeoylshikimic acid
MBS57910103-O-Caffeoylshikimic acid
TRC-C843760-100MGtrans-3-O-Caffeoylshikimic Acid
MBS3617728-015-O-Cinnamoylquinic acid
TRC-C899975-50MG5-O-Coumaroylquinic Acid
AB19995-O-Feruloylquinic acid

Popular Products