Carnosic acid

Base Information

• Chemical Name: Carnosic acid
• CAS No.: 3650-09-7
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44
• Hs Code.: 29182900
• European Community (EC) Number: 609-253-7
• NSC Number: 694080
• UNII: LI791SXT24
• DSSTox Substance ID: DTXSID20904450
• Nikkaji Number: J16.357K
• Wikipedia: Carnosic_acid
• Wikidata: Q412827
• Metabolomics Workbench ID: 63999
• ChEMBL ID: CHEMBL484853
• Mol file: 3650-09-7.mol

Synonyms:carnosic acid;salvin

Chemical Property of Carnosic acid

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 4.45E-11mmHg at 25°C
• Melting Point: 190°C(lit.)
• Refractive Index: 1.575
• Boiling Point: 506.4 °C at 760 mmHg
• PKA: 4.14±0.40(Predicted)
• Flash Point: 274.2 °C
• PSA: 77.76000
• Density: 1.184 g/cm³
• LogP: 4.31610
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 332.19875937
• Heavy Atom Count: 24
• Complexity: 500

Purity/Quality:

Carnosic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1=C(C(=C2C(=C1)CCC3C2(CCCC3(C)C)C(=O)O)O)O
• Isomeric SMILES: CC(C)C1=C(C(=C2C(=C1)CC[C@@H]3[C@@]2(CCCC3(C)C)C(=O)O)O)O
• Description: Carnosic acid (salvin) is abundant in sage and rosemary leaves. It has antioxidative, anti-carcinogenic, anti-inflammatory, anti-microbial, anti-adipogenic, antiproliferative, antitumorigenic and neuroprotective properties. It is increasingly exploited within food, nutrition health, and cosmetic industries. It is used as the main active antioxidants of food additives in Europe, in products including oils, animal fats, sauces, bakery wares, meat, and fish products etc. to prevent oxidation and prolong their storage time. It is proven to be efficient in the treatment of hyperglycemia. In cosmetic industry, it is used in the hair care and skin care products. Oral health care is another cosmetics-related application of carnosic acid: in vitro studies have shown that it efficiently protected against typical cariogenic microorganisms. It is the important raw material of tooth grinding and gargle agent.
• Uses: Carnosic Acid is a phenolic component of rosemary. It acts as a potent antioxdant and also has UV protective activity. Specifically protection for UV-A radiation and damage. Carnosic Acid also inhibits the free-radical chain reaction that leads to the oxidation of fats and oils, thereby stabilizing and increasing the shelf life of meats.

Technology Process of Carnosic acid

There total 3 articles about Carnosic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

(+)-Pisiferic acid (67494-15-9) → carnosic acid (3650-09-7,139236-75-2)

Guidance literature:

(+)-Pisiferic acid; With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; chloroform; at 20 ℃; for 1h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; chloroform; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1248/cpb.58.27

Reference yield:

11-carnosyl m-chlorobenzoate → carnosic acid (3650-09-7,139236-75-2)

Guidance literature:

With sodium tetrahydroborate; sodium hydroxide; In methanol; water; for 2h; Reflux;

DOI:10.1248/cpb.58.27

Reference yield:

→ carnosic acid (3650-09-7,139236-75-2)

Guidance literature:

upstream raw materials:

(+)-Pisiferic acid

Downstream raw materials:

carnosol

carnosol

carnosic acid quinone

Refernces