ChemFOnt: Showing chemical card for Angelic acid (CFc000010842)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:58:25 UTC

Chemfont ID

CFc000010842

Molecule Identification

Common Name

Angelic acid

Definition

Angelic acid is found in fats and oils. Angelic acid is a constituent of Angelica archangelica (angelica) Angelic acid has a double bond between the second and third carbons of the chain. Together with tiglic acid form a pair of cis-trans isomers. Angelic acid is a volatile body, of biting acid taste and pungent sour odour. It crystallizes in colorless monoclinic prisms. Angelic acid was formerly used therapeutically as a sedative. Angelic acid is a monocarboxylic unsaturated organic acid. It is found in garden angelica (Angelica archangelica), Umbelliferae, and many other plants. It was also isolated from the defensive secretion of certain carabid beetles

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Z)-2-Methylcrotonic acid	ChEBI
2-Methyl-2Z-butenoic acid	ChEBI
2-Methylisocrotonic acid	ChEBI
Acide angelique	ChEBI
Acido angelico	ChEBI
alpha-Methylisocrotonic acid	ChEBI
Angelicasaeure	ChEBI
Angelikasaeure	ChEBI
cis-2,3-Dimethylacrylic acid	ChEBI
cis-2-Dimethylcrotonic acid	ChEBI
cis-2-Methyl-2-butenoic acid	ChEBI
Z-2-Methyl-2-butenoic acid	ChEBI
Z-2-Methylcrotonic acid	ChEBI
(Z)-2-Methylcrotonate	Generator
2-Methyl-2Z-butenoate	Generator
2-Methylisocrotonate	Generator
a-Methylisocrotonate	Generator
a-Methylisocrotonic acid	Generator
alpha-Methylisocrotonate	Generator
Α-methylisocrotonate	Generator
Α-methylisocrotonic acid	Generator
cis-2,3-Dimethylacrylate	Generator
cis-2-Dimethylcrotonate	Generator
cis-2-Methyl-2-butenoate	Generator
Z-2-Methyl-2-butenoate	Generator
Z-2-Methylcrotonate	Generator
Angelate	Generator
(2Z)-2-Methylbut-2-enoic acid	HMDB
(Z)-2-Methyl-2-butenoic acid	HMDB
2-Methyl-(2Z)-2-butenoic acid	HMDB
2-Methyl-(Z)-2-butenoic acid	HMDB
2-Methyl-(Z)-crotonic acid	HMDB
2-Methyl-2-butenoic acid, cis	HMDB
alpha-Methyl isocrotonic acid	HMDB
Crotonic acid, 2-methyl-, (Z)- (8ci)	HMDB
(2Z)-2-Methyl-2-butenoic acid	HMDB
(Z)-2-Methylbut-2-enoic acid	HMDB
(Z)-2-Methylbutenoic acid	HMDB
Angelic acid	HMDB
cis-alpha,beta-Dimethylacrylic acid	HMDB
cis-α,β-Dimethylacrylic acid	HMDB
Tiglate	Generator

Chemical Formula

C₅H₈O₂

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

IUPAC Name

(2Z)-2-methylbut-2-enoic acid

Traditional Name

angelic acid

CAS Registry Number

565-63-9

SMILES

C\C=C(\C)C(O)=O

InChI Identifier

InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-

InChI Key

UIERETOOQGIECD-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-methylbut-2-enoic acid (CHEBI:36431 )
Branched fatty acids (LMFA01020029 )

Functional Ontology

Physiological effect

Organoleptic effect

Odor

Spicy

Disposition

Biological location

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0029608)

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Lovage (FooDB: FOOD00100)

Herbs and Spices (FooDB: FOOD00866)

Tea

Vegetable

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Other vegetable

Giant butterbur (FooDB: FOOD00314)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Fruit

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Endogenous (HMDB: HMDB0029608)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Sedative (HMDB: HMDB0029608)

Physical Properties

Predicted Properties

Property	Value	Source
logP	1.32	ChemAxon
pKa (Strongest Acidic)	4.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.32 m³·mol⁻¹	ChemAxon
Polarizability	10.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon