AFCDB: (E)-Aconitic acid (FDB008305)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:01 UTC

Update date

2019-11-26 03:02:26 UTC

Primary ID

FDB008305

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(E)-Aconitic acid

Description

Isolated from Asarum europaeum, from cane-sugar molasses, roasted chicory root, roasted malt barley, passion fruit, sorghum root and sugar beet. Flavouring agent used in fruit flavours and alcoholic beverages. Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerisation of citrate to isocitrate in the citric acid cycle. It is acted upon by aconitase. Trans-aconitate in the urine is a biomarker for the consumption of soy products. (E)-Aconitic acid is found in many foods, some of which are cereals and cereal products, rice, garden tomato (variety), and root vegetables.

CAS Number

4023-65-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.72 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	-0.52	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.23 m³·mol⁻¹	ChemAxon
Polarizability	13.96 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H6O6

IUPAC name

(1E)-prop-1-ene-1,2,3-tricarboxylic acid

InChI Identifier

InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+

InChI Key

GTZCVFVGUGFEME-HNQUOIGGSA-N

Isomeric SMILES

OC(=O)C\C(=C/C(O)=O)C(O)=O

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

Classification

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aconitic acid (CHEBI:32806 )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 41.39%; H 3.47%; O 55.14%	DFC
Melting Point	Mp 194-195° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa2 4.46 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000f-9100000000-814aded0eac117ddb550	2015-03-01	View Spectrum
GC-MS	(E)-Aconitic acid, 3 TMS, GC-MS Spectrum	splash10-003s-3971000000-d4adfdbddf5dc3badb47	Spectrum
GC-MS	(E)-Aconitic acid, non-derivatized, GC-MS Spectrum	splash10-003s-3971000000-d4adfdbddf5dc3badb47	Spectrum
GC-MS	(E)-Aconitic acid, non-derivatized, GC-MS Spectrum	splash10-0002-1930000000-1043e640a069e4ed3c64	Spectrum
Predicted GC-MS	(E)-Aconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06w9-4900000000-38239492ad0e66d6533b	Spectrum
Predicted GC-MS	(E)-Aconitic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9167000000-07ccdac5775cc3e75c95	Spectrum
Predicted GC-MS	(E)-Aconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-1f04239a9a7133f89d08	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000f-9000000000-49f5c2a7959cfbbbe09f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000f-9100000000-d4857c30b96cf4786dbe	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00b9-1900000000-51343d1269f884535cca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9100000000-b3ebe9a6fedcb9608872	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-2d6b96d6e5ed92f0fdee	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000l-9000000000-d36114a1c7a0318b1f7a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-f4ae4a72d5f2beed9106	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9200000000-49eaf4d6558839930e52	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00b9-1900000000-51343d1269f884535cca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9100000000-b3ebe9a6fedcb9608872	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-4f60fbd245c1d58cd7d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000l-9000000000-d36114a1c7a0318b1f7a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-f4ae4a72d5f2beed9106	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9200000000-49eaf4d6558839930e52	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9100000000-a70cb799a63ff364ca21	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9000000000-eabb8ab38f98bb81b1ee	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9200000000-2d22108854c0dad1b598	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9300000000-3cf209c9f766f6c0efe8	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-8e26562af9ae45eb3303	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02di-1900000000-7fec32a5e34c3b55d683	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01w0-9600000000-ee172c3013370ab0da31	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-1900000000-18635ce5a20ce1b78139	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-2900000000-58bb75a2a1b28dbffd73	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rf-9300000000-19df730d01f07fcf6573	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

32806

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00958

CRC / DFC (Dictionary of Food Compounds) ID

DFV04-S:DFV05-T

EAFUS ID

Not Available

Dr. Duke ID

TRANS-ACONITIC-ACID

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1001681

SuperScent ID

Not Available

Wikipedia ID

Aconitic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti feedant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
vegetable	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nut	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
toasted	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

(E)-Aconitic acid (FDB008305)

Structure for FDB008305 ((E)-Aconitic acid)