carminic acid

Base Information

• Chemical Name: carminic acid
• CAS No.: 476-39-1
• Molecular Formula: C₂₂H₂₀O₁₃
• Molecular Weight: 492.393
• Mol file: 476-39-1.mol

Synonyms:7-Glucopyranosyl-3,5,6,8-tetrahydroxyl-1-methyl-9,10-dioxoanthracene-2-carboxylic acid;C000386

Chemical Property of carminic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of carminic acid

There total 8 articles about carminic 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: 100.0%

3,5,6,8-Tetraacetoxy-1-methyl-9,10-dioxo-7-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-9,10-dihydro-anthracene-2-carboxylic acid (76173-05-2) → Carminic acid (1260-17-9,476-39-1)

Guidance literature:

With hydrogenchloride; In ethanol; for 1h; Heating;

DOI:10.1039/a705145j

Reference yield:

D-glucose (50-99-7) → Carminic acid (1260-17-9,476-39-1)

Guidance literature:

With engineered Escherichia coli strain BAP₁ harboring antDEFBG (encoding type II polyketide synthase from Photorhabdus luminescens), zhuIJ (encoding cyclases from Streptomyces sp. R₁₁₂₈), dnrF[P₂₁₇K] (encoding aklavinone 12-hydroxylase[P₂₁₇K] from Streptomyces peucetius), and GtCGT[V₉₃Q/Y₁₉₃F] (encoding UDP-glucosyltransferase[V₉₃Q/Y₁₉₃F] from Gentiana triflora), with overexpression of Corynebacterium glutamicum accBCD₁; In aq. phosphate buffer; at 30 ℃; pH=6.8; Reagent/catalyst; Microbiological reaction;

DOI:10.1021/jacs.0c12406

Reference yield:

3-Acetoxy-1-methyl-5,8,9,10-tetraoxo-7-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-5,8,9,10-tetrahydro-anthracene-2-carboxylic acid → Carminic acid (1260-17-9,476-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄, Pb(OAc)4

2: 100 percent / aq. HCl / ethanol / 1 h / Heating

With lead(IV) acetate; hydrogenchloride; sulfuric acid; In ethanol;

DOI:10.1039/a705145j

upstream raw materials:

3,5,6,8-Tetraacetoxy-1-methyl-9,10-dioxo-7-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-9,10-dihydro-anthracene-2-carboxylic acid

3,5,8-Trihydroxy-1-methyl-9,10-dioxo-7-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-9,10-dihydro-anthracene-2-carboxylic acid

D-glucose

Downstream raw materials:

1-methylanthraquinone

9,10-phenanthrenequinone

Refernces

• 1、 Zaima, Kazumasa,Fukamachi, Azusa,Yagi, Ryoko,Ito, Yusai,Sugimoto, Naoki,Akiyama, Hiroshi,Shinomiya, Kazufusa,Harikai, Naoki. "Kinetic study of the equilibration between carminic acid and its two isomers isolated from cochineal dye". . p. 306 - 310. Retrieved 2017/03/15.
• 2、 Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela,Fiecchi, Alberto,Scala, Antonio,et al.. "The First Total Synthesis of Carminic Acid". . p. 1319 - 1320. Retrieved 2007/10/02.