Products for Research Use Only
RegisterLogin

1-Caffeoylquinic acid

CAT: 0804-HY-N0460-01Size: 1 mgDry Ice: NoHazardous: No
Product image 1
1 / 1
CAT#:0804-HY-N0460-01Size:1 mg
Selected
24/48H Stock Items & 2 to 6 Weeks non Stock Items.
Quick Request Actions
Description
1-Caffeoylquinic acid is an effective NF-κB inhibitor, shows significant binding affinity to the RH domain of p105 with Ki of 0.007 μM[1]. 1-Caffeoylquinic acid has anti-oxidative stress ability[2]. 1-Caffeoylquinic acid is the Inhibitor for PD-1/PD-L1[3].
CAS Number
1241-87-8
UNSPSC
12352005
Target
NF-κB; PD-1/PD-L1
Type
Natural Products
Related Pathways
Immunology/Inflammation; NF-κB
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/1-caffeoylquinic-acid.html
Purity
99.54
Solubility
DMSO : 250 mg/mL (ultrasonic)
Smiles
O[C@@H]1[C@H](O)C[C@@](OC(/C=C/C2=CC(O)=C(O)C=C2)=O)(C(O)=O)C[C@H]1O
Molecular Formula
C16H18O9
Molecular Weight
354.31
References & Citations
[1]Khan MK, et al. Dietary phytochemicals as potent chemotherapeutic agents against breast cancer: Inhibition of NF-κB pathway via molecular interactions in rel homology domain of its precursor protein p105. Pharmacogn Mag. 2013 Jan;9 (33) :51-7.|[2]Jiang Y, et al. Caffeoylquinic acid derivatives rich extract from Gnaphalium pensylvanicum willd. Ameliorates hyperuricemia and acute gouty arthritis in animal model. BMC Complement Altern Med. 2017 Jun 17;17 (1) :320.|[3]Han Y, et al. PD-1/PD-L1 inhibitor screening of caffeoylquinic acid compounds using surface plasmon resonance spectroscopy. Anal Biochem. 2018 Apr 15;547:52-56.|[4]Sun Y, et al., Qualitative and quantitative analysis of phenolics in Tetrastigma hemsleyanum and their antioxidant and antiproliferative activities. J Agric Food Chem. 2013 Nov 6;61 (44) :10507-15.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Npc233393

1-O-caffeoylquinic acid is an alkyl caffeate ester obtained by the formal condensation of the carboxy group of trans-caffeic acid with the 1-hydroxy group of ()-quinic acid. It has a role as a Camellia sinensis metabolite, an antioxidant, an antineoplastic agent and a NF-kappaB inhibitor. It is a quinic acid and an alkyl caffeate ester. It is functionally related to a trans-caffeic acid. It derives from a hydride of a (-)-quinic acid.

CAS Number1241-87-8
PubChem CID10155076
IUPAC Nametrans-(3R,5R)-1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4,5-trihydroxycyclohexane-1-carboxylic acid
Molecular FormulaC16H18O9
Molecular Weight354.31
XLogP-0.4
Topological Polar Surface Area165
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Heavy Atom Count25
Formal Charge0
Complexity520
SMILES
C1[C@H](C([C@@H](CC1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O)O
InChI
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-16(15(23)24)6-11(19)14(22)12(20)7-16/h1-5,11-12,14,17-20,22H,6-7H2,(H,23,24)/b4-2+/t11-,12-,14?,16?/m1/s1
InChIKey
GWTUHAXUUFROTF-AVXJPILUSA-N
Chemical Structure
2D Structure
2D structure of Npc233393
CAS: 1241-87-8
CID: 10155076
Formula: C16H18O9
MW: 354.31
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight354.31
XLogP3-0.4
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Exact Mass354.09508215
Monoisotopic Mass354.09508215
Topological Polar Surface Area165 Ų
Heavy Atom Count25
Formal Charge0
Complexity520
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Related Products

CatalogName
HY-N10044-013-Feruloyl-4-caffeoylquinic acid
HY-N4168-013-O-Caffeoylquinic acid methyl ester
HY-N110774,5-Di-O-caffeoylquinic acid
HY-W046704-011-Methoxycyclopropanecarboxylic acid
HY-1627361-Piperazinehexanoic acid
HY-W005540-011-Cyclopentenecarboxylic acid
HY-W713926-011-Pyrenedecanoic acid
HY-W103047-011-Pyrenebutyric acid
HY-D0293Acid Blue 1
HY-18570-011-Naphthaleneacetic acid

Alternative Products

CatalogName
3786991-Caffeoylquinic acid
AB00945-Caffeoylquinic acid
AB00954-Caffeoylquinic acid
FC177962-013-O-Caffeoylquinic acid
433290-014-O-Caffeoylquinic Acid
2998415-Caffeoylquinic acid/Neochlorogenic acid
2998324-Caffeoylquinic acid/Cryptochlorogenic acid
A12036-204-O-Caffeoylquinic acid 20mg
BUP05422-013-Feruloyl-4-caffeoylquinic acid

Popular Products