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Chemical Structure| 3650-09-7 Chemical Structure| 3650-09-7
Chemical Structure| 3650-09-7

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Carnosic Acid is a naturally occuring benzenediol abietane diterpene found in rosemary, possessing antioxidative and antimicrobial properties.

Synonyms: Salvin

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Product Details of Carnosic acid

CAS No. :3650-09-7
Formula : C20H28O4
M.W : 332.43
SMILES Code : O=C([C@]12CCCC(C)(C)[C@]1([H])CCC3=C2C(O)=C(O)C(C(C)C)=C3)O
Synonyms :
Salvin
MDL No. :MFCD02259459
InChI Key :QRYRORQUOLYVBU-VBKZILBWSA-N
Pubchem ID :65126

Safety of Carnosic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Carnosic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3650-09-7 ]

[ 3650-09-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 3650-09-7 ]
  • [ 5957-80-2 ]
YieldReaction ConditionsOperation in experiment
Example 3; 13. Ig rosemary extract (containing 43% carnosic acid and 18% carnosol ), 6Og acetic acid and 13 mg of iron(III) chloride hexahydrate where stirred under a nitrogen blanket. At 15C was slowly added 2.9 ml hydrogen peroxide 35% in water. The mixture was stirred for 1.5 h at 15C followed by addition of ImI hydrochloric acid 37%. The mixture was stirred for 18h at ambient. The slurry was filtered and washed with 10 ml acetic acid. The crystallisate was dried in the vacuum at 700C. We obtained 5.57g carnosol of 92% purity. Yield = 65%.
  • 2
  • [ 3650-09-7 ]
  • [ 5957-80-2 ]
  • 11,20-dihydroxy-12-methoxyabiet-8,11,13-triene [ No CAS ]
  • 11,12,16,17-tetrahydroxy-7,10-(epoxymethano)abiet-8,11,13-triene-20-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Nocardia sp. NRRL 5646; In DMF (N,N-dimethyl-formamide); water; at 28 - 121℃; for 24.0h;pH 7.0;biotransformation; Enzymatic reaction; Analytical-Scale Biotransformation. A two-stage fermentation protocol was used for analytical and preparative scale formation of carnosic acid metabolites. The medium contained 0.5% (w/v) soybean meal, 0.5% yeast extract, 0.5% NaCl, 0.5% K2HPO4, and 2% dextrose per 1 L of distilled water, adjusted to pH 7.0 with 6 N HCl, was autoclaved at 121 C. for 15 min. Analytical incubations were conducted in 25 mL of sterile medium held in 125 mL stainless steel-capped Delong culture flasks that were incubated with shaking at 250 rpm at 28 C. on a New Brunswick Scientific, Innova 5000 Gyrotory three-tier shaker. A 10% inoculum derived from 72 h old stage I cultures was used to initiate stage II cultures, which were incubated for 24 h more before receiving 5 mg of carnosic acid in 0.2 mL of N,N-dimethylformamide, and incubations were continued. Substrate controls consisted of sterile medium and substrate incubated under the same conditions but without microorganism. Samples of 3 mL were withdrawn for analysis at 24, 48, 72, and 144 h after substrate addition, extracted with 1 mL of EtOAc. The organic layer was separated from aqueous medium by centrifugation at 1,200×g in a desktop centrifuge and 30 muL samples were spotted onto TLC plate developed with solvent system A. On the basis of screening experiments, three metabolites were reproducibly formed by Nocardia with Rf values of 0.88 for Compound 4, 0.71 for Compound 5 and 0.54 for Compound 6. [0022] Preparative Biotransformation of Carnosic Acid. Nocardia cultures were incubated as before in ten, 125 mL stainless steel-capped Delong culture flasks, each containing 25 mL of medium. Carnosic acid (100 mg) was dissolved in 1 mL N,N-dimethylformamide and evenly distributed among the 24 h-old stage-II cultures. After 72 h, the contents of 10 flasks were combined and centrifuged at 10,000×g at 4 C. for 20 min. The supernatant (225 mL) was extracted with three 500 mL volumes of EtOAc. The organic layers were pooled, dried over anhydrous Na2SO4, filtered through sintered glass, and vacuum-concentrated to yield 93 mg of a viscous brown residue. [0023] Isolation of Metabolites. The brown residue was subjected to Si gel flash column chromatography (1.5×50 cm) using in sequence, Hexane/EtOAC (95:5?75:25). Two fractions, A (22 mg) and B (53 mg), were obtained based on TLC analysis. Fractions A and B were separately resolved by reversed phase, Sepralyte C18 Si gel flash column chromatography (1×50 cm), using a MeOH-H2O gradient solvent system (40?70%) under column pressures of 0.28 kg/cm2, at a flow rate of 2 mL/min while 3 mL fractions were collected. Final sample purifications were carried out with Sephadex LH-20 (25-150 mum. Pharmacia Fine Chemical Co.) columns eluted with MeOH:CHCl3 (1:1) to afford carnosic acid metabolites Compound 4 (10.5 mg), Compound 5 (38 mg), and Compound 6 (8 mg).
 

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