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Rosmarinic acid

CAT: 1568-C09455-1gSize: 1 gDry Ice: YesHazardous: No
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CAT#:1568-C09455-1gSize:1 g
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CAS Number
20283-92-5
Synonyms
Rosemary acid
Target
Complement System
Applications
Immunology & Inflammation
Smiles
C1=CC (=C (C=C1CC (C (=O) O) OC (=O) C=CC2=CC (=C (C=C2) O) O) O) O
Molecular Formula
C18H16O8
Additionnal Information
Rosmarinic acid (RA, Rosemary acid) is a naturally occurring hydroxylated compound. It has the ability to block complement fixation, inhibit lipoxygenase and cyclooxygenase activity and inhibit the expression of CCL11 and CCR3 by suppressing the IKK-β activity in NF-κB activation signaling.
Storage Conditions
2 years -80 in solvent

Chemical Information

Rosmarinic Acid

(R)-rosmarinic acid is a stereoisomer of rosmarinic acid having (R)-configuration. It has a role as a geroprotector and a plant metabolite. It is a conjugate acid of a (R)-rosmarinate. It is an enantiomer of a (S)-rosmarinic acid.

CAS Number20283-92-5
PubChem CID5281792
IUPAC Name(2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
Molecular FormulaC18H16O8
Molecular Weight360.3
XLogP2.4
Topological Polar Surface Area145
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Heavy Atom Count26
Formal Charge0
Complexity519
SMILES
C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChI
InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1
InChIKey
DOUMFZQKYFQNTF-WUTVXBCWSA-N
Chemical Structure
2D Structure
2D structure of Rosmarinic Acid
CAS: 20283-92-5
CID: 5281792
Formula: C18H16O8
MW: 360.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight360.3
XLogP32.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass360.08451746
Monoisotopic Mass360.08451746
Topological Polar Surface Area145 Ų
Heavy Atom Count26
Formal Charge0
Complexity519
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
TRC-R684800-5GRosmarinic Acid

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