ChemFOnt: Showing chemical card for Aspirin (CFc000001251)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:50 UTC

Chemfont ID

CFc000001251

Molecule Identification

Common Name

Aspirin

Definition

Aspirin is only found in individuals who have consumed this drug. Aspirin or acetylsalicylic acid (acetosal) is a drug in the family of salicylates, often used as an analgesic (against minor pains and aches), antipyretic (against fever), and anti-inflammatory. It has also an anticoagulant effect and is used in long-term low-doses to prevent heart attacks and cancer. It was isolated from meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839. While their extract was somewhat effective, it also caused digestive problems such as irritated stomach and diarrhoea, and even death when consumed in high doses. In 1853, a French chemist named Charles Frederic Gerhardt neutralized salicylic acid by buffering it with sodium (sodium salicylate) and acetyl chloride, creating acetosalicylic anhydride. Gerhardt's product worked, but he had no desire to market it and abandoned his discovery. In 1897, researcher Arthur Eichengrun and Felix Hoffmann, a research assistant at Friedrich Bayer & Co. in Germany, derivatized one of the hydroxyl functional groups in salicylic acid with an acetyl group (forming the acetyl ester), which greatly reduced the negative effects. This was the first synthetic drug, not a copy of something that existed in nature, and the start of the pharmaceuticals industry. The name 'aspirin' is composed of a- (from the acetyl group) -spir- (from the plant genus Spiraea) and -in (a common ending for drugs at the time). It has also been stated that the name originated by another means. As referring to AcetylSalicylic and 'pir' in reference to one of the scientists who was able to isolate it in crystalline form, Raffaele Piria. Finally 'in' due to the same reasons as stated above. Salicylic acid (which is a naturally occurring substance found in many plants) can be acetylated using acetic anhydride, yielding aspirin and acetic acid as a byproduct. It is a common experiment performed in organic chemistry labs, and generally tends to produce low yields due to the relative difficulty of its extraction from an aqueous state. The trick to getting the reaction to work is to acidify with phosphoric acid and heat the reagents under reflux with a boiling water bath for between 40 minutes and an hour. Aspirin acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(ACETYLOXY)benzoIC ACID	ChEBI
2-Acetoxybenzenecarboxylic acid	ChEBI
2-Acetoxybenzoic acid	ChEBI
Acetylsalicylate	ChEBI
Acetylsalicylsaeure	ChEBI
Acide 2-(acetyloxy)benzoique	ChEBI
Acide acetylsalicylique	ChEBI
Acido acetilsalicilico	ChEBI
Acidum acetylsalicylicum	ChEBI
ASA	ChEBI
Azetylsalizylsaeure	ChEBI
Easprin	ChEBI
O-Acetoxybenzoic acid	ChEBI
O-Acetylsalicylic acid	ChEBI
O-Carboxyphenyl acetate	ChEBI
Salicylic acid acetate	ChEBI
Acetylsalicylic acid	Kegg
Aspalon	Kegg
Durlaza	Kegg
2-(ACETYLOXY)benzoate	Generator
2-Acetoxybenzenecarboxylate	Generator
2-Acetoxybenzoate	Generator
O-Acetoxybenzoate	Generator
O-Acetylsalicylate	Generator
O-Carboxyphenyl acetic acid	Generator
Salicylate acetate	Generator
Salicylic acid acetic acid	Generator
2-Carboxyphenyl acetate	HMDB
Acenterine	HMDB
Acetard	HMDB
Aceticyl	HMDB
Acetol	HMDB
Acetonyl	HMDB
Acetophen	HMDB
Acetosal	HMDB
Acetosalin	HMDB
Acetylin	HMDB
Acetyonyl	HMDB
Acetysal	HMDB, MeSH
Acetysalicylic acid	HMDB
Acylpyrin	HMDB, MeSH
Asatard	HMDB
Aspergum	HMDB
Aspirdrops	HMDB
Benaspir	HMDB
Bialpirinia	HMDB
Bufferin	HMDB
Caprin	HMDB
Cardioaspirina	HMDB
Ecolen	HMDB
Ecotrin	HMDB, MeSH
Empirin	HMDB
Endosprin	HMDB, MeSH
Endydol	HMDB
O-(Acetyloxy)benzoate	HMDB
O-(Acetyloxy)benzoic acid	HMDB
Persistin	HMDB
Pharmacin	HMDB
Polopiryna	HMDB, MeSH
Premaspin	HMDB
Rheumintabletten	HMDB
Rhodine	HMDB
Salcetogen	HMDB
Saletin	HMDB
Salospir	HMDB
Solprin	HMDB, MeSH
Solprin acid	HMDB
Solpyron	HMDB
Tasprin	HMDB
Temperal	HMDB
Toldex	HMDB
Triaminicin	HMDB
Magnecyl	MeSH, HMDB
Polopirin	MeSH, HMDB
Solupsan	MeSH, HMDB
Zorprin	MeSH, HMDB
Dispril	MeSH, HMDB
Aloxiprimum	MeSH, HMDB
Colfarit	MeSH, HMDB
Micristin	MeSH, HMDB
Acid, acetylsalicylic	MeSH, HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

2-(acetyloxy)benzoic acid

Traditional Name

aspirin

CAS Registry Number

50-78-2

SMILES

CC(=O)OC1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)

InChI Key

BSYNRYMUTXBXSQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylsalicylic acids

Alternative Parents

Substituents

Acylsalicylic acid
Phenol ester
Benzoic acid
Phenoxy compound
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

salicylates (CHEBI:15365 )
acetate ester (CHEBI:15365 )
benzoic acids (CHEBI:15365 )

Functional Ontology

Physiological effect

Health effect

Observation

Nervous system disorder

Coma (HMDB: HMDB0001879)

Central nervous system disorder

Reye's syndrome (HMDB: HMDB0001879)

Circulatory system disorder

Blood and lymphatic system disorder

Hypoglycemia (HMDB: HMDB0001879)

Vascular disorder

Hypotension (HMDB: HMDB0001879)

Renal system and urinary system

Renal disorder

Renal failure (HMDB: HMDB0001879)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17646136)

Cell

Hematocyte

Platelet (HMDB: HMDB0001879)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001879)

Cellular substructure

Cytoplasm (HMDB: HMDB0001879)
Extracellular (HMDB: HMDB0001879)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001879)

Source

Exogenous

Exogenous (HMDB: HMDB0001879)

Food

Food (HMDB: HMDB0001879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0001879)

Endogenous

Plant

Plant (HMDB: HMDB0001879)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Acetylsalicylic Acid Pathway (HMDB: HMDB0001879)
Acetylsalicylic Acid Action Pathway (HMDB: HMDB0001879)
Acetylsalicylic Acid Action Pathway (HMDB: HMDB0001879)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.46 g/L	ALOGPS
logP	1.43	ALOGPS
logP	1.24	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.45 m³·mol⁻¹	ChemAxon
Polarizability	17.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon