(2R)-3-(3,4-dihydroxyphenyl)-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid

• ChemBase ID: 145291
• Molecular Formular: C18H16O8
• Molecular Mass: 360.31484
• Monoisotopic Mass: 360.08451747
• SMILES: c1cc(c(cc1C[C@H](C(=O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)O)O
• Canonical SMILES: O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c(c1)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)/t16-/m1/s1
• InChIKey: DOUMFZQKYFQNTF-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-(3,4-dihydroxyphenyl)-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid; (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid
• IUPAC Traditional name: (2R)-3-(3,4-dihydroxyphenyl)-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid; rosemary acid
• Synonyms: (R)-O-(3,4-Dihydroxycinnamoyl)-3-(3,4- dihydroxyphenyl)lactic acid; 3,4-Dihydroxycinnamic acid (R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethyl ester; Rosmarinic acid; (R)-O-(3,4-二羟基肉桂酰)-3-(3,4-二羟苯基)乳酸; 3,4-二羟基肉桂酸 (R)-1-羧基-2-(3,4-二羟苯)乙酯; 迷迭香酸

Database IDs

• CAS Number: 20283-92-5
• MDL Number: MFCD00017740
• Beilstein Number: 2227587
• PubChem SID: 24878185; 162239498
• PubChem CID: 5281792

CALCULATED PROPERTIES

• Acid pKa: 3.1312933
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.66241366
• LogD (pH = 7.4): -0.46487963
• Log P: 3.0041263
• Molar Refractivity: 90.9501 cm^3
• Polarizability: 34.615208 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Oil
• Melting Point: 171-175 °C; 171-175 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... LCK(3932)

Product Information

• Purity: ≥95.0% (HPLC); 96%
• Grade: primary reference standard; purum
• Empirical Formula (Hill Notation): C18H16O8

DETAILS

Sigma Aldrich - 536954

Biochem/physiol Actions
Rosmarinic acid has shown to contain antioxidant, anti-inflammatory and antimicrobial activities. Possesses promising physiological actions related to cognitive performance, Alzheimer′s disease prevention, kideney disease treatment, cardioprotection and cancer chemoprevention.
Packaging
5 g in glass bottle

Sigma Aldrich - 44699

Biochem/physiol Actions
Rosmarinic acid has shown to contain antioxidant, anti-inflammatory and antimicrobial activities. Possesses promising physiological actions related to cognitive performance, Alzheimer′s disease prevention, kideney disease treatment, cardioprotection and cancer chemoprevention.

Sigma Aldrich - 00390580

Application
Reference standard in the analysis of herbal medicinal products.
Biochem/physiol Actions
Rosmarinic acid has shown to contain antioxidant, anti-inflammatory and antimicrobial activities. Possesses promising physiological actions related to cognitive performance, Alzheimer′s disease prevention, kideney disease treatment, cardioprotection and cancer chemoprevention.
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate