33383-55-0

Basic information

• Product Name: (E)-trans-(+)-Chrysanthemumdicarboxylic acid
• Synonyms: (1S)-3β-[(E)-2-Carboxy-1-propenyl]-2,2-dimethylcyclopropane-1α-carboxylic acid;(E)-trans-(+)-Chrysanthemumdicarboxylic acid;3β-[(E)-2-Carboxy-1-propenyl]-2,2-dimethylcyclopropane-1α-carboxylic acid;(1R)-2,2-Dimethyl-3α-[(E)-2-carboxy-1-propenyl]cyclopropane-1β-carboxylic acid;(1R,3R)-2,2-Dimethyl-3-[(E)-3-hydroxy-2-methyl-3-oxo-1-propenyl]cyclopropanecarboxylic acid;trans-Chrysanthemumdicarboxylic acid
• CAS NO: 33383-55-0
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 0
• Mol File: 33383-55-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 378.5°C at 760 mmHg
• Flash Point: 196.9°C
• Appearance: /
• Density: 1.315g/cm³
• Vapor Pressure: 8.95E-07mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: (E)-trans-(+)-Chrysanthemumdicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-trans-(+)-Chrysanthemumdicarboxylic acid(33383-55-0)
• EPA Substance Registry System: (E)-trans-(+)-Chrysanthemumdicarboxylic acid(33383-55-0)

Safety Data

• Hazardous Substances Data: 33383-55-0(Hazardous Substances Data)

Usage

General Description

(E)-trans-(+)-Chrysanthemumdicarboxylic acid is a naturally occurring organic compound found in the Chrysanthemum plant species. It is also known as Chrysanthemum acid and can be extracted from the flowers of these plants. Chemically, this compound is a form of dicarboxylic acid, which contains two carboxyl or COOH functional groups. These groups give the molecule its acidic properties. As a result, it exhibits typical carboxylic acid behavior, including the ability to donate protons and form hydrogen bonds, and can participate in various biochemical reactions. (E)-trans-(+)-Chrysanthemumdicarboxylic acid has been studied for its potential applications in cosmetic products due to its safety profile, biodegradability, and biocompatibility.

InChI:InChI=1/C10H14O4/c1-5(8(11)12)4-6-7(9(13)14)10(6,2)3/h4,6-7H,1-3H3,(H,11,12)(H,13,14)/b5-4+/t6-,7+/m0/s1

Upstream product

• 497-95-0 (+/-)-3t-(3t-carboxy-2,2-dimethyl-cycloprop-r-yl)-2-methyl-acrylic acid 
• 92464-14-7 (E)-3-((1S,3S)-3-Formyl-2,2-dimethyl-cyclopropyl)-2-methyl-acrylic acid 
• 72079-89-1 (E)-3-((1S,3R)-3-Formyl-2,2-dimethyl-cyclopropyl)-2-methyl-acrylic acid methyl ester 
• 72079-86-8 methyl 4,6-O-(phenylmethylene)-2,3-dideoxy-2,3-C-isopropylidene-α-D-mannopyranoside 
• 72079-84-6 methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-C--α-D-mannopyranoside 
• 72079-85-7 methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-C--α-D-mannopyranoside 
• 72079-83-5 methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-C--α-D-mannopyranoside 
• 92464-12-5 methyl 4,6-O-benzylidene-2,3-dideoxy-2,3-C--α-D-mannopyranoside 
• 92464-13-6 methyl (E)-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methyl-D-manno-oct-2-(E)-enoate 
• 72079-87-9 4,6-O-benzylidene-2,3-dideoxy-2,3-C-isopropylidene-aldehydo-D-mannose 
• 72079-88-0 methyl 6,8-O-benzylidene-2,3,4,5-tetradeoxy-4,5-C-isopropylidene-2-C-methtyl-D-manno-oct-2-(E)-enoate 
• 623-73-4 diazoacetic acid ethyl ester 
• 42415-57-6 ethyl 2,5-dimethylhexa-2,4-dienoate2,5-dimethylsorbate 

Downstream Products

• 936-87-8 trans-caronic acid 
• 936-87-8 (1S,2R)-3,3-Dimethyl-cyclopropane-1,2-dicarboxylic acid 
• 22467-83-0 (+/-)-3t-(3t-methoxycarbonyl-2,2-dimethyl-cycloprop-r-yl)-2-methyl-acrylic acid methyl ester 

Relevant articles and documents

ANNULATED PYRANOSIDES-V. AN ENANTIOSPECIFIC ROUTE TO (+) AND (-) CHRYSANTHENUM DICARBOXYLIC ACIDS.

Methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside undergoes the Wadsworth-Emmons cyclopropanation with phosphonopropionate to give a cyclopropyl carboxylate which is processed to give the gem-dimethylcyclopropano pyranoside.The glycosylic acetal of this substance is readily hydrolyzed by boiling water, and the resulting cis-cyclopropane carboxaldehyde may epimerized quantitatively to the trans-analog by treatment with sodium methoxide.These are now converted into the (+)- and (-)-chrysanthenum dicarboxylic acids, respectively, by the same sequence of reactions involving (a) olefination with methyl 2-(triphenylphosphoranylidene)propionate, (b) hydrolysis of the benzylidene ring and cleavage of the resulting triol with sodium metaperiodate, and (c) oxidation of the resulting aldehyde with silver I oxide.In the case of the (+)-enantiomer the last reaction is preceeded by epimerization.The overall yields from the D-allopyranoside are respectively 27percent, in 10 steps for the (+)-enantiomer, and 24percent, in 10 steps for the (-)-enantiomer, from the known epoxide 7.