Bipolar trans carotenoid salts and their uses

A technology of carotene and polar groups, applied in the field of bipolar trans carotenoid salt compounds

Inactive Publication Date: 2006-10-04
DIFFUSION PHARMA LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, crocetin is only slightly soluble in water

Method used

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  • Bipolar trans carotenoid salts and their uses
  • Bipolar trans carotenoid salts and their uses
  • Bipolar trans carotenoid salts and their uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Synthesis of trans sodium crocetin

[0123]

[0124] By adding a symmetric C with a conjugated carbon-carbon double bond 10 Trans-sodium crocetin was synthesized by coupling dialdehyde with [3-methoxy-2-buten-1-ylidene]triphenylphosphorane. This product was then saponified with NaOH / methanol solution.

[0125] Triphenylphosphine (trephenylphosphine, concentration about 2 mol / L) dissolved in ethyl acetate was slowly added to ethyl bromoacetate. After isolation and treatment with base, the product can be treated with iodomethane followed by treatment with base to form the phosphorane. In this case, the basic compound to form the carotenoid skeleton can be prepared starting from a cyclic compound such as furan. Furan reacts with bromine and methanol followed by a selective deprotonation step to form monoaldehydes. The monoaldehyde is then coupled with the phosphorane. Acidic conditions deprotect other dimethyl acetal groups to provide free aldehydes. This compound...

Embodiment 2

[0257] Synthesis of potassium trans-norbixinate

[0258]

[0259] By adding a symmetric C with a conjugated carbon-carbon double bond 20 The dialdehyde is coupled with [1-(carboethoxy)methylene]triphenylphosphorane to form trans-norcarmine potassium. This compound was prepared analogously to the preparation previously listed for trans-sodium crocetin, except that the starting material furan was replaced with the appropriate ring structure. This product was then saponified with KOH / methanol solution.

Embodiment 3

[0261] Synthesis of longer BTCS

[0262]

[0263] By adding a symmetric C with a conjugated carbon-carbon double bond 10 Dialdehyde was added to an excess of [3-methoxy-2-buten-1-ylidene]triphenylphosphorane to synthesize the above compound. This compound was prepared analogously to the preparation previously listed for trans-sodium crocetin, except that the starting material furan was replaced with the appropriate ring structure. The trans 40-carbon product is then isolated using procedures such as chromatography. This product was then saponified with NaOH / methanol solution.

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PUM

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Abstract

The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.

Description

technical field [0001] The present invention relates to bipolar trans carotenoid salt compounds, their dissolution method, their preparation method and their use method. These bipolar trans carotenoid salt (BTCS) compounds are beneficial in increasing the diffusivity of oxygen between red blood cells and body tissues in mammals, including humans. Background technique [0002] Carotenoids are a class of hydrocarbons consisting of isoprenoid units linked in the center of the molecule in such a way that their arrangement is reversed. The main chain (skeleton) of the molecule consists of conjugated carbon-carbon double and single bonds, and may also have side groups. Although the skeleton of carotenoids was once thought to contain 40 carbons, it has been recognized for a long time that carotenoids can also have carbon skeletons containing fewer than 40 carbon atoms. The 4 single bonds surrounding the carbon-carbon double bond are all in the same plane. If the side groups are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/00A01N37/00C07C57/13C07C67/343C07F9/09C07F9/113
CPCC07F9/098C07C57/13C07F9/113C07C67/343A61P11/00A61P11/06A61P25/00A61P25/28A61P35/00A61P43/00A61P9/00A61P9/10A61P3/10C07C69/602C07F1/04C07F1/00
Inventor 约翰·L·盖纳雷蒙德·C·格拉比克
Owner DIFFUSION PHARMA LLC
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