Rosmarinic acid CAS#20283-92-5
(R)-rosmarinic acid is a high-purity chiral stereoisomer of natural rosmarinic acid, featuring a unique and stable R-type stereochemical configuration that distinguishes its molecular spatial structure from conventional racemic rosmarinic acid. As a naturally occurring and biologically active secondary plant metabolite widely derived from Labiatae botanical species, this compound possesses outstanding inherent biological properties and stable molecular activity, laying a solid foundation for various biomedical and cosmetic research applications.
It is scientifically defined as the conjugate acid form of (R)-rosmarinate, exhibiting reversible acid-base transformation characteristics in different solution environments with excellent chemical stability under standard storage conditions.
In terms of chiral characteristics, (R)-rosmarinic acid serves as the exclusive enantiomeric counterpart of (S)-rosmarinic acid. The two isomers differ significantly in spatial conformation, which further leads to distinct differences in molecular affinity, bioabsorption efficiency and functional activity in biological systems.
Beyond its basic metabolic characteristics, this monomer delivers prominent geroprotective efficacy, effectively alleviating cellular oxidative stress, delaying cellular senescence progression, and protecting biological tissues from damage caused by long-term free radical erosion.
With high chiral purity and low impurity content, standardized (R)-rosmarinic acid is an ideal high-precision research raw material and functional additive.
It is widely applicable for chiral mechanism research, structure-activity relationship analysis, anti-aging basic experiments, and natural bioactive compound screening, providing reliable and consistent quality support for pharmaceutical development, cosmetic formulation optimization and biological academic research.
Rosmarinic acid Chemical Properties |
Melting point | 171-175 °C (lit.) |
alpha | +102～+110°(D/20℃)(c=0.2,C2H5OH) |
Boiling point | 694.7±55.0 °C(Predicted) |
density | 1.33 |
storage temp. | 2-8°C |
solubility | Soluble in ethanol, DMSO or dimethyl formamide to approximately 25 mg/mL. |
pka | 2.78±0.10(Predicted) |
form | powder |
color | white to faintly beige |
biological source | Rosemarinus officinalis L. |
Water Solubility | H2O: 1mg/mL, clear, colorless |
BRN | 2227587 |
Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. |
Cosmetics Ingredients Functions | ANTIOXIDANT |
InChI | InChI=1/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-/s3 |
InChIKey | DOUMFZQKYFQNTF-WUTVXBCWSA-N |
SMILES | C(C1C=CC(O)=C(O)C=1)[C@H](C(=O)O)OC(=O)/C=C/C1C=CC(O)=C(O)C=1 |&1:9,r| |
LogP | 0.871 (est) |
CAS DataBase Reference | 20283-92-5(CAS DataBase Reference) |
Safety Information |
Hazard Codes | T |
Risk Statements | 25 |
Safety Statements | 45 |
WGK Germany | 3 |
RTECS | GD8990000 |
F | 10-23 |
HS Code | 29189900 |
Storage Class | 11 - Combustible Solids |
Rosmarinic acid belongs to a class of naturally‑sourced phenolic bioactive substances, which demonstrates remarkable antioxidant and anti‑inflammatory bioactivities for multiple experimental research scenarios. In biological assay tests, this compound can achieve 90 % inhibition rate against lipid peroxidation within rat liver microsomes when applied at the concentration of 25 μg/mL. It is capable of restraining endotoxin‑triggered complement system activation, meanwhile mitigating the accompanying generation of prostacyclin that mediates inflammatory responses. Besides, rosmarinic acid can effectively block the biosynthesis of 5‑HETE and LTB4 originating from human polymorphonuclear leukocytes (PMNL), with the effective working concentration ranging from 10‑5 M to 10‑3 M. These observable pharmacological features render it a preferred test substance for inflammation‑related mechanism exploration, antioxidant efficacy evaluation and natural‑derived active‑ingredient screening projects.
Regarding shipment arrangement, flexible fast‑delivery options are available to satisfy customers’ varying project timelines. Stock‑available orders can be dispatched within 2‑3 working days upon order confirmation. For batches requiring fresh manufacturing, the full production cycle will take roughly 7‑10 working days before goods are ready for shipment. Relevant supporting documents such as COA and MSDS will be provided together to facilitate your laboratory testing and import clearance procedures.
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