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16110-51-3

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16110-51-3 Usage

Description

Cromolyn is a synthetic analog of the plant extract khellin that was first developed in the late 1960s and introduced into clinical practice the following decade. It is continued to be used widely in the treatment of allergic rhinitis, asthma, mastocytosis, and conjunctivitis. It has an outstanding safety profile and can be readily obtained without prescription in many countries.

Uses

Different sources of media describe the Uses of 16110-51-3 differently. You can refer to the following data:
1. It is used for bronchial asthma, as well as prevention of seasonal, constant, and physically caused asthma attacks and allergic rhinitis.
2. Cromolyn is used primarily for the prophylaxis of various types of asthma and in the treatment of allergic rhinitis, mastocytosis, and vernal conjunctivitis.

Definition

ChEBI: A dicarboxylic acid that is the bis-chromone derivative of glycerol. It is effective as a mast cell stabilizer.

Therapeutic Function

Bronchodilator

General Description

Solid.

Air & Water Reactions

Water soluble.

Reactivity Profile

Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Cromoglicic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat.

Fire Hazard

Flash point data for Cromoglicic acid are not available. Cromoglicic acid is probably combustible.

Mechanism of action

Cromolyn stabilizes the membranes of mast cells, stopping the release of allergy mediators and suppressing activation of eosinophiles, neutrophilis, thrombocytes, and macrophages, which take part in the formation of bronchospasms. Cromylyn differs from the majority of medications taken for obstructive diseases of the respiratory tract in that it is used only as a preventative agent.

Clinical Use

Cromolyn generally is used prophylactically for bronchial asthma (as an inhaled powder), for prevention of exercise-induced bronchospasm, and for seasonal and perennial allergic rhinitis (nasal solution). Topically, it also is used as eye drops for allergic conjunctivitis and keratitis. In the management of asthmatic conditions, it is administered using a power-operated nebulizer. The bioavailability is very low with oral administration because of poor absorption. By inhalation, the powder is irritating to some patients. After inhalation, much less than 10% of the dose reaches the systemic circulation. An oral dosage form is used for mastocytosis.

Synthesis

Cromolyn, 5,5[(2-hydroxytrimethylen)dioxy] bis 4-oxo-4H-1-benzopiran-2- carboxylic acid (23.3.9), are synthesized by reacting 2,6-dihydroxyacetophenone with epichlorohydrine, during which the chlorine atom in epichlorohydrine is replaced and an opening of the epoxide ring takes place, resulting in a bis-product 23.3.7. Cyclization of this product into a bis-derivative 23.3.8 is accomplished using diethyloxalate, subsequent alkaline hydrolysis of the ester groups of which gives the desired cromolyn (23.3.9).

Environmental Fate

The major prophylactic effect of cromolyn is centered on inhibition of the degranulation of pulmonary mast cells causing a reduction in histamine release, reduced leukotriene production, and inhibition of release of inflammatory mediators from several cell types.

Toxicity evaluation

Cromolyn is a mast cell stabilizer and typically marketed as the sodium salt in the United States. It is typically found in solution as a clear and colorless liquid. Cromolyn is soluble in water and the solution is completely soluble in water.

Check Digit Verification of cas no

The CAS Registry Mumber 16110-51-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,1,1 and 0 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 16110-51:
(7*1)+(6*6)+(5*1)+(4*1)+(3*0)+(2*5)+(1*1)=63
63 % 10 = 3
So 16110-51-3 is a valid CAS Registry Number.
InChI:InChI=1/C23H16O11/c24-11(9-31-12-4-5-16-13(6-12)14(25)7-19(33-16)22(27)28)10-32-17-2-1-3-18-21(17)15(26)8-20(34-18)23(29)30/h1-8,11,24H,9-10H2,(H,27,28)(H,29,30)

16110-51-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name cromoglycic acid

1.2 Other means of identification

Product number -
Other names Acidum cromoglicicum

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16110-51-3 SDS

16110-51-3Synthetic route

disodium cromoglicate
15826-37-6

disodium cromoglicate

cromoglicinic acid
16110-51-3

cromoglicinic acid

Conditions
ConditionsYield
With hydrogenchloride In water pH=3;66%
With hydrogenchloride In water pH=3;66%
With hydrogenchloride In water at 20℃; pH=2;
disodium cromoglicate
15826-37-6

disodium cromoglicate

A

cromoglicinic acid
16110-51-3

cromoglicinic acid

B

[(2-hydroxytrimethylene)dioxy]bis(4-oxo-4H-1-benzopyran-2-carboxylic acid)

[(2-hydroxytrimethylene)dioxy]bis(4-oxo-4H-1-benzopyran-2-carboxylic acid)

Conditions
ConditionsYield
In disodium salt of cromolyn
cromoglicinic acid
16110-51-3

cromoglicinic acid

tert-butyl N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)carbamate
194920-62-2

tert-butyl N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)carbamate

C38H46N2O15
936098-08-7

C38H46N2O15

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;67%
cromoglicinic acid
16110-51-3

cromoglicinic acid

N,N-dimethylformamide di-tert-butyl acetal
36805-97-7

N,N-dimethylformamide di-tert-butyl acetal

5,5’-[(2-hydroxy-1,3-propanediyl)bis(oxy)]bis[4-oxo-4H-1-benzopyran-2-carboxylic acid di-tert-butyl ester]

5,5’-[(2-hydroxy-1,3-propanediyl)bis(oxy)]bis[4-oxo-4H-1-benzopyran-2-carboxylic acid di-tert-butyl ester]

Conditions
ConditionsYield
In toluene Reflux;30%
cromoglicinic acid
16110-51-3

cromoglicinic acid

disodium cromoglycate-3,3'-d2

disodium cromoglycate-3,3'-d2

Conditions
ConditionsYield
With water-d2; sodium hydrogencarbonate; rhodium(III) chloride 1.) dioxane, reflux, 12 h; Multistep reaction;
methanol
67-56-1

methanol

cromoglicinic acid
16110-51-3

cromoglicinic acid

1,3-bis(2-methoxycarbonylchromon-5-yloxy)propan-2-ol
51471-26-2

1,3-bis(2-methoxycarbonylchromon-5-yloxy)propan-2-ol

Conditions
ConditionsYield
With hydrogenchloride Heating;
cromoglicinic acid
16110-51-3

cromoglicinic acid

acetic anhydride
108-24-7

acetic anhydride

O-Acetyl-cromoglicinsaeure

O-Acetyl-cromoglicinsaeure

Conditions
ConditionsYield
for 1h; Heating;
cromoglicinic acid
16110-51-3

cromoglicinic acid

5-(8,10-Dimethyl-9,11-dioxo-8,9,10,11-tetrahydro-2H-pyrano[4',3',2':4,5]chromeno[2,3-d]pyrimidin-2-yliden)-1,3-dimethyl-hexahydro-2,4,6-pyrimidintrion

5-(8,10-Dimethyl-9,11-dioxo-8,9,10,11-tetrahydro-2H-pyrano[4',3',2':4,5]chromeno[2,3-d]pyrimidin-2-yliden)-1,3-dimethyl-hexahydro-2,4,6-pyrimidintrion

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1 h / Heating
2: 0.034 g / acetic acid; acetic anhydride / 1.5 h / Heating
View Scheme
cromoglicinic acid
16110-51-3

cromoglicinic acid

C27H22O12

C27H22O12

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / Heating
2: acetic acid / 1.5 h / Heating
View Scheme
cromoglicinic acid
16110-51-3

cromoglicinic acid

5,5'-(2-Hydroxypropan-1,3-diyldioxy)bis{4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-4-pyrazolyl)imino]-4H-chromen-2-carbonsaeuremethylester}-tetraperchlorat

5,5'-(2-Hydroxypropan-1,3-diyldioxy)bis{4-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-4-pyrazolyl)imino]-4H-chromen-2-carbonsaeuremethylester}-tetraperchlorat

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / Heating
2: 7.8 percent / aq. HClO4 / methanol / 0.83 h / Heating
View Scheme
cromoglicinic acid
16110-51-3

cromoglicinic acid

octanol
111-87-5

octanol

C31H32O11
927888-29-7

C31H32O11

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane at 20℃;
triisopropanolamine
122-20-3

triisopropanolamine

cromoglicinic acid
16110-51-3

cromoglicinic acid

cromoglycic acid triisopropanolamine salt

cromoglycic acid triisopropanolamine salt

Conditions
ConditionsYield
at 80℃; for 0.5h;
cromoglicinic acid
16110-51-3

cromoglicinic acid

5,5’-[(2-[l8F]fluoro-1,3-propanediyl)bis(oxy)]bis[4-oxo-4H-1-benzopyran-2-carboxylic acid di-tert-butyl ester]

5,5’-[(2-[l8F]fluoro-1,3-propanediyl)bis(oxy)]bis[4-oxo-4H-1-benzopyran-2-carboxylic acid di-tert-butyl ester]

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene / Reflux
2: dmap; pyridine / 18 h / 0 - 25 °C
3: 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosan/[18F]fluoride / dimethyl sulfoxide / 0.17 h / 130 °C
View Scheme

16110-51-3Upstream product

16110-51-3Relevant articles and documents

METHOD OF SCREENING COMPOUND USEFUL IN TREATING ALLERGIC DISEASE

-

Page/Page column 7-8, (2010/04/30)

The present invention provides a method of screening for a compound useful for treatment of an allergic disease by identifying a molecule targeted by Intal upon exertion of its efficacy as an anti-allergic agent (hereinafter referred as a target) and using the target, as well as a new type of anti-allergic agent comprising a compound obtainable by the screening as an active ingredient for treatment of an allergic disease.

NOVEL DRUG DISCOVERY TARGET AND MEDICINE ACTING ON THE SAME

-

Page/Page column 12-13, (2008/06/13)

The present invention provides a pharmaceutical composition comprising as an active ingredient a compound that specifically binds to MFP-2 or a functional fragment thereof and a screening method for the compound; the compound and a pharmaceutical composition comprising the same are highly useful as anti-inflammatory agents and anti-allergic agents.

LIPOSOMAL COMPOSITIONS

-

, (2008/06/13)

-

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