595-29-9

Basic information

• Product Name: (1R,3S)-(-)-CAMPHORIC ANHYDRIDE
• Synonyms: (1R,3S)-(-)-CAMPHORIC ANHYDRIDE;(1R)-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione;CAMPHORACIDANHYDRIDE;(1R,3S)-(-)-Camphoric anhydride, 98+%;(1R)-Camphoric acid anhydride;(1R,5S)-1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
• CAS NO: 595-29-9
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• EINECS: 209-860-3
• Mol File: 595-29-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 223°C (dec.)
• Boiling Point: 270 ºC at 760 mmHg
• Flash Point: 121.1 ºC
• Appearance: /
• Density: 1.137 g/cm3
• Vapor Pressure: 0.00702mmHg at 25°C
• Refractive Index: 1.487
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: (1R,3S)-(-)-CAMPHORIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S)-(-)-CAMPHORIC ANHYDRIDE(595-29-9)
• EPA Substance Registry System: (1R,3S)-(-)-CAMPHORIC ANHYDRIDE(595-29-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 595-29-9(Hazardous Substances Data)

Usage

General Description

(1R,3S)-(-)-Camphoric anhydride is a chemical compound with the molecular formula C10H14O3. It is a derivative of camphor and is classified as an anhydride, meaning it is formed from the removal of water from two carboxylic acid molecules. (1R,3S)-(-)-CAMPHORIC ANHYDRIDE is known for its use as a chiral building block in the synthesis of pharmaceuticals and agrochemicals. It has a unique three-dimensional structure, which makes it valuable for use in organic chemistry reactions. Additionally, (1R,3S)-(-)-Camphoric anhydride is of research interest for its potential biological activity and its use as a chiral auxiliary in asymmetric synthesis.

InChI:InChI=1/C10H14O3/c1-9(2)6-4-5-10(9,3)8(12)13-7(6)11/h6H,4-5H2,1-3H3/t6-,10?/m1/s1

Upstream product

• 91-22-5 quinoline 
• 560-07-6 (1S,3S)-(+)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid 
• 60-29-7 diethyl ether 
• 2767-84-2 Camphorquinone 
• 64-19-7 acetic acid 
• 112924-25-1 Bromcamphersaeureanhydrid 
• 10334-26-6 (R)-camphorquinone 
• 7722-84-1 dihydrogen peroxide 
• 7719-09-7 thionyl chloride 
• 29607-02-1 (1R,3S)-3-(methoxycarbonyl)-1,2,2-trimethylcyclopentanecarboxylic acid 
• 14487-70-8 3-diazocamphor 
• 75-05-8 acetonitrile 
• 368423-74-9 (1R)-cis-camphoric acid-3-ethyl ester 
• 75-36-5 acetyl chloride 

Downstream Products

• 2321-07-5 fluorescein 
• 112989-27-2 (1R)-1.2.2-trimethyl-cyclopentane-dicarboxylic acid-(1r.3c)-3-((Ξ)-1-p-tolyl-ethyl ester) 
• 98179-01-2 (1R)-3-benzyloxy-1,8,8-trimethyl-3-aza-bicyclo[3.2.1]octane-2,4-dione 
• 306935-16-0 1,2,2-trimethyl-cyclopentane-1,3-dicarboxylic acid-1-methyl ester 
• 306935-15-9 α-Methylhydrogen-dl-isocamphersaeure 
• 108207-39-2 (1R)-3-(2-methoxy-phenyl)-1,8,8-trimethyl-3-aza-bicyclo[3.2.1]octane-2,4-dione 
• 197236-38-7 1,2,2-trimethyl-3-p-tolylcarbamoyl-cyclopentanecarboxylic acid 

Relevant articles and documents

Synthesis of cyclic D-(+)-camphoric acid imides and study of their antiviral activity

[Figure not available: see fulltext.] Several D-(+)-camphoric acid imides, not previously described in the literature, were synthesized with good yields. The synthesis of previously known imides was improved. The cytotoxicity and antiviral activity of all synthesized imides were studied.

Composition comprising camphoric acid derivative and application of composition in cosmetics

The invention provides a composition containing a camphoric acid derivative and application of the composition in cosmetics, and belongs to the technical field of cosmetics. A preparation method of the camphoric acid derivative comprises the following steps: converting camphoric acid into camphoric anhydride, and carrying out N-acylation reaction on the camphoric anhydride and amino acid, and synthesizing to obtain the camphoric acid derivative. The invention also discloses application of the composition containing the camphoric acid derivative in cosmetics. According to the preparation methodof the camphoric acid derivative, the amino acid is introduced into a camphoric acid molecular skeleton, water solubility and cell permeability of camphoric acid can be effectively changed, a novel camphoric acid-based bioactive compound is synthesized, the obtained camphoric acid derivative has a good protection effect on ESF-1 cell senescence caused by UV damage, and skin lesion such as skin thickening and wrinkle generation caused by UV irradiation can be improved.

Modified McFadyen-Stevens reaction for a versatile synthesis of aliphatic/aromatic aldehydes: Design, optimization, and mechanistic investigations

The traditional McFadyen-Stevens reaction requires harsh alkaline reaction conditions, thus precluding application to the synthesis of aliphatic aldehydes. Our modified McFadyen-Stevens reaction enables the transformation from the N,N-acylsulfonyl hydrazine to the corresponding aldehyde upon treatment with an imidazole-TMS imidazole combination without relying on oxidative or reductive reagents. The reduced basicity and in situ protection of the resulting aldehyde widens the substrate scope to include aliphatic aldehydes, even ones bearing an α-hydrogen atom. Close examination of the side reactions for particular substrates in combination with theoretical considerations via DFT calculations led to a mechanistic understanding of the McFadyen-Stevens reaction involving an acyl diazene and a hydroxy carbene as reasonable intermediates.