CARNOSOL CAS 5957-80-2

Introduction：Basic information about CARNOSOL CAS 5957-80-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

CARNOSOL Basic information

• Product Name: CARNOSOL
• Synonyms: 1,3,4,9,10,10AS-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISO-PROPYL-2H-9S,4AR-(EPOXYMETHANO)PHENANTHREN-12-ONE;1,3,4,9,10AS-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISO-PROPYL-2H-9S,4AR-(EPOXYMETHANO)PHENANTHREN-12-ONE;1,2,3,4,4A,9,10,10AS-OCTAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISOPROPYL-9S, 4AR (EPOXYMETHANO)PHENANTHREN-12-ONE;CARNOSOL(RG);CARNOSOL;Carnosol, froM RoseMarinus officinalis;Carnosol, 98%, from Rosemarinus officinalis;2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,9S,10aS)-
• CAS: 5957-80-2
• MF: C20H26O4
• MW: 330.42
• Product Categories: chemical reagent;pharmaceutical intermediate;Miscellaneous Natural Products;Antioxidant;Biochemicals Found in Plants;Nutrition Research;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 5957-80-2.mol

CARNOSOL Chemical Properties

• Melting point: 240～242℃
• Boiling point: 524.8±50.0 °C(Predicted)
• density: 1.26±0.1 g/cm3(Predicted)
• storage temp.: Sealed in dry,Store in freezer, under -20°C
• solubility: DMSO:66.0(Max Conc. mg/mL);199.74(Max Conc. mM)
• form: Solid
• pka: 8.91±0.40(Predicted)
• color: White
• biological source: Rosemarinus officinalis L. leaves
• Major Application: food and beverages
• InChI: InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1
• InChIKey: XUSYGBPHQBWGAD-PJSUUKDQSA-N
• SMILES: C1(C)(C)[C@@]2([H])[C@]3(C(=O)O[C@@]([H])(C2)C2=C3C(O)=C(O)C(C(C)C)=C2)CCC1
• LogP: 2.832 (est)

Safety Information

• Safety Statements: 24/25
• WGK Germany: 3
• HS Code: 29322090
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Skin Sens. 1
• Hazardous Substances Data: 5957-80-2(Hazardous Substances Data)

CARNOSOL Usage And Synthesis

Description

Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.

Description

Carnosol is a phenol that has been found in rosemary (R. officinalis) and has diverse biological activities. It decreases nitric oxide (NO) production in mouse peritoneal exudate macrophages when used at concentrations ranging from 6 to 25 μM. Carnosol scavenges peroxyl and hydroxyl radicals and inhibits lipid peroxidation in cell-free assays. It inhibits 5-lipoxygenase (5-LO; IC₅₀ = 0.1 μM for the recombinant human enzyme) and the synthesis of leukotrienes in human polymorphonuclear leukocytes (PMNs; IC₅₀ = 7 μM). In vivo, carnosol (200 mg/kg) reduces mammary DNA adduct formation and tumorigenesis in a rat model of DMBA-induced mammary tumorigenesis.

Chemical Properties

White powder

Uses

Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.

Definition

ChEBI: Carnosol is a diterpenoid.

Cytotoxicity

IC₅₀ (μg/mL): 65 (HL-60), 58 (K562), 50(Hep G2), 48 (MCF-7), 53 (MOLT-4)(Farimani et al. 2012)
IC₅₀ (μg/mL): 61.46 (AGS) (Areche et al.2009)
IC₅₀ (μg/mL): 2 (P388) (Aoyagi et al.2006)
IC₅₀ (μg/mL): 1.19 (A2780), 3.30(SW1573), 8.59 (WiDr), 7.93 (T-47D),1.29 (HBL-100) (Guerrero et al. 2006).

Synthesis

Take 2000g of dried rosemary branches and leaves, add 14L of petroleum ether, reflux extraction for 3 times, 3 hours each time, merge the 3 extracts, concentrate and recover the petroleum ether, get the extract; dissolve the extract with 40% ethanol, filter to remove insoluble matter, get 1000ml of mother liquor as adsorbent, adsorb the adsorbent with 500ml of D101 large pore adsorbent resin, adsorb and then elute the eluent with 1000ml of purified water, and then elute with 1500ml of 90% ethanol. Elution, and then eluted with 1500 ml of 90% ethanol solution, the eluent is divided into 6 sections, combined with the middle 4; combined eluent concentrated to 100 ml under reduced pressure, add 200 ml of water, stir to precipitate, and leave for 3 hours; centrifuged to get the precipitate containing sage bitter endolipids; precipitate dissolved with 200 ml of ethyl acetate, to which 200 ml of petroleum ether was added, stirring, precipitate precipitate; filtered to get the Sage bitter endolipid crude product, the crude product with 800 ml of anhydrous ethanol crystallization, to get the sage bitter endolipid crystals; filtration, drying, to get the crystals 13.6 g, HPLC detection of sage bitter endolipid content of 96.1%.

References

[1] MARION MAN-YING CHAN  Hsing I H  Chi Tang Ho. Effects of three dietary phytochemicals from tea, rosemary and turmeric on inflammation-induced nitrite production[J]. Cancer letters, 1995, 96 1: Pages 23-29. DOI: 10.1016/0304-3835(95)03913-h
[2] O I ARUOMA. Antioxidant and pro-oxidant properties of active rosemary constituents: carnosol and carnosic acid.[J]. Xenobiotica, 1992, 22 2: 257-268. DOI: 10.3109/00498259209046624
[3] DANIEL POECKEL . Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes[J]. Biochemical pharmacology, 2008, 76 1: Pages 91-97. DOI: 10.1016/j.bcp.2008.04.013
[4] KEITH SINGLETARY  Matthew W  Christopher MacDonald. Inhibition by rosemary and carnosol of 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis and in vivo DMBA-DNA adduct formation[J]. Cancer letters, 1996, 104 1: Pages 43-48. DOI: 10.1016/0304-3835(96)04227-9

CARNOSOL Preparation Products And Raw materials

• Preparation Products: EPIROSMANOL-->Rosmanol