(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

Base Information

• Chemical Name: (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
• CAS No.: 5957-80-2
• Molecular Formula: C20H26O4
• Molecular Weight: 330.424
• Hs Code.: 29322090
• NSC Number: 39143
• DSSTox Substance ID: DTXSID30863665
• Wikidata: Q104667593
• Mol file: 5957-80-2.mol

Synonyms:(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one;NSC-39143;MEGxp0_001119;SCHEMBL18290355;DTXSID30863665;XUSYGBPHQBWGAD-UHFFFAOYSA-N;HMS3649B03;(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one;BCP20030;NSC39143;SMP2_000248;FT-0689376;SR-01000946633;SR-01000946633-1;11,12-Dihydroxy-7,20-epoxyabieta-8(14),9(11),12-trien-20-one;(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.0^{1,10.0^{2,7]hexadeca-2,4,6-trien-15-one;3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

Chemical Property of (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

Chemical Property:

• Appearance/Colour: White to beige solid.
• Vapor Pressure: 1.24E-11mmHg at 25°C
• Melting Point: 240～242℃
• Refractive Index: 1.606
• Boiling Point: 524.8 °C at 760 mmHg
• PKA: 8.91±0.40(Predicted)
• Flash Point: 187 °C
• PSA: 66.76000
• Density: 1.26 g/cm³
• LogP: 4.28690
• Storage Temp.: −20°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 330.18310931
• Heavy Atom Count: 24
• Complexity: 542

Purity/Quality:

99% ^*data from raw suppliers

Carnosol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C(=C2C(=C1)C3CC4C2(CCCC4(C)C)C(=O)O3)O)O
• Description: Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen. 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.
• Uses: Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.

Technology Process of (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one

There total 8 articles about (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one 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: 100.0%

carnosic acid (3650-09-7,139236-75-2) → carnosol (5957-80-2)

Guidance literature:

With oxygen; In acetone; at 20 ℃; for 4h; under 75.0075 Torr;

DOI:10.1021/np010565o

Reference yield: 65.0%

carnosic acid; carnosol; mixture of → carnosol (5957-80-2,7067-14-3)

Guidance literature:

With oxygen; sodium hydrogencarbonate; water; In carbon dioxide; at 20 - 60 ℃; for 48h; under 71257.1 - 120012 Torr; Product distribution / selectivity;

Reference yield:

carnosic acid (3650-09-7,139236-75-2) → carnosol (5957-80-2) + 11,20-dihydroxy-12-methoxyabiet-8,11,13-triene + 11,12,16,17-tetrahydroxy-7,10-(epoxymethano)abiet-8,11,13-triene-20-one

Guidance literature:

Nocardia sp. NRRL 5646; In DMF (N,N-dimethyl-formamide); water; at 28 - 121 ℃; for 24h; pH=7; biotransformation; Enzymatic reaction;

upstream raw materials:

carnosic acid

Downstream raw materials:

11,12-Di-O-methylcarnosol

11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester

epi-rosmanol

galdosol

Refernces

• 1、 Tada, Masahiro,Ohkanda, Tomoyuki,Kurabe, Jun. "Syntheses of carnosic acid and carnosol, anti-oxidants in rosemary, from pisiferic acid, the major constituent of Sawara". experimental part. p. 27 - 29. Retrieved 2010/04/26.
• 2、 -. "PROCESS FOR PRODUCING CARNOSOL FROM CARNOSIC ACID". Page/Page column 11. . Retrieved 2009/05/28.