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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:45 UTC

Update Date

2023-02-21 17:20:43 UTC

HMDB ID

HMDB0031512

Secondary Accession Numbers

HMDB31512

Metabolite Identification

Common Name

Tiglic aldehyde

Description

Tiglic aldehyde is found in animal foods. Tiglic aldehyde is isolated from chives (Allium schoenoprasum). Also present in onion, tomato, cheeses, Scotch, spearmint oil, tangerine peel oil, cooked chicken and other foods. Tiglic aldehyde is a flavour ingredient trans-2-Methyl-2-butenal is an organic compound with the formula CH3CH=C(CH3)CHO. This colorless liquid is a building block in organic synthesis. It is an , -unsaturated aldehyde related to the better known crotonaldehyde

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2E)-2-Methyl-2-butenal	HMDB
(e)-2-Methyl-2-butenal	HMDB, MeSH
(e)-2-Methylbut-2-en-1-al	HMDB
(e)-2-Methylbut-2-enal	HMDB
(e)-2-Methylcrotonaldehyde	HMDB
2-Methyl-(2E)-2-butenal	HMDB
2-Methyl-(e)-2-butenal	HMDB
2-Methyl-(e)-crotonaldehyde	HMDB
2-Methyl-2(e)-butenal	HMDB
2-Methyl-2-butenal	HMDB, MeSH
2-Methyl-2-butenal, (e)	HMDB
2-Methyl-2-butenal, trans	HMDB
2-Methyl-crotonaldehyde	HMDB
2-Methylbut-(e)-2-enal	HMDB
CH3CH=C(CH3)cho	HMDB
Crotonaldehyde, 2-methyl-, (e)- (8ci)	HMDB
e-2-Methyl-2-butenal	HMDB
FEMA 3407	HMDB
Tiglaldehyde	HMDB
Tiglaldehyde (2-methyl-2-butenal)	HMDB
Tiglic acid aldehyde	HMDB
Tiglinaldehyde	HMDB
trans-2,3-Dimethylacrolein	HMDB
trans-2-Methyl-2-butenal	HMDB
trans-2-Methylcrotonaldehyde	HMDB
trans-Tigaldehyde	HMDB
trans-Tiglaldehyde	HMDB
2-Methylbut-2-enal	MeSH

Chemical Formula

C₅H₈O

Average Molecular Weight

84.1164

Monoisotopic Molecular Weight

84.057514878

IUPAC Name

(2Z)-2-methylbut-2-enal

Traditional Name

(2Z)-2-methylbut-2-enal

CAS Registry Number

497-03-0

SMILES

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

InChI Identifier

InChI=1S/C5H8O/c1-3-5(2)4-6/h3-4H,1-2H3/b5-3-

InChI Key

ACWQBUSCFPJUPN-HYXAFXHYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enals

Alternative Parents

Substituents

Enal
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0031512)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0031512)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031512)

Source

Endogenous

Endogenous (HMDB: HMDB0031512)

Plant

Plant (HMDB: HMDB0031512)

Animal

Animal (HMDB: HMDB0031512)

Exogenous

Food

Food (HMDB: HMDB0031512)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)

Fruit vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Herb and spice

Oilseed crop

Safflower (FooDB: FOOD00042)

Herb

Spearmint (FooDB: FOOD00112)
Welsh onion (FooDB: FOOD00241)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031512)

Role

Biological role

Energy storage (HMDB: HMDB0031512)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031512)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	117.00 to 118.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	25 mg/mL	Not Available
LogP	1.065 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	40.6 g/L	ALOGPS
logP	0.93	ALOGPS
logP	1.16	ChemAxon
logS	-0.32	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.4 m³·mol⁻¹	ChemAxon
Polarizability	9.49 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	118.556	31661259
DarkChem	[M-H]-	112.543	31661259
DeepCCS	[M+H]+	121.774	30932474
DeepCCS	[M-H]-	119.878	30932474
DeepCCS	[M-2H]-	155.367	30932474
DeepCCS	[M+Na]+	129.907	30932474
AllCCS	[M+H]+	121.4	32859911
AllCCS	[M+H-H2O]+	116.9	32859911
AllCCS	[M+NH4]+	125.6	32859911
AllCCS	[M+Na]+	126.8	32859911
AllCCS	[M-H]-	125.4	32859911
AllCCS	[M+Na-2H]-	130.1	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tiglic aldehyde	C\C=C(\C)C=O	1070.0	Standard polar	33892256
Tiglic aldehyde	C\C=C(\C)C=O	708.7	Standard non polar	33892256
Tiglic aldehyde	C\C=C(\C)C=O	739.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tiglic aldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-05q9-9000000000-c55d49861ee6b1113cf9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiglic aldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiglic aldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 10V, Positive-QTOF	splash10-000i-9000000000-1e63e408fa4731465f7d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 20V, Positive-QTOF	splash10-000i-9000000000-840489df070350dbd21a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 40V, Positive-QTOF	splash10-0pb9-9000000000-967f72345ff4e63b646f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 10V, Negative-QTOF	splash10-001i-9000000000-07023e058e96a5079eca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 20V, Negative-QTOF	splash10-0a59-9000000000-8c33b9aae6f9f2e3d24a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 40V, Negative-QTOF	splash10-0a4i-9000000000-073297c5c61a3fcdc6fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 10V, Positive-QTOF	splash10-00kr-9000000000-27b60b169c7619ca2071	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 20V, Positive-QTOF	splash10-0aou-9000000000-7c06bdab5a64b26afeb3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 40V, Positive-QTOF	splash10-052u-9000000000-9c99b9d9eaf8c956daec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 10V, Negative-QTOF	splash10-001i-9000000000-1fe8bbf8f6ab17ae0b2b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 20V, Negative-QTOF	splash10-0f89-9000000000-a76c812630dace829064	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglic aldehyde 40V, Negative-QTOF	splash10-014i-9000000000-2f7bb8956d818712b876	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008105

KNApSAcK ID

C00058120

Chemspider ID

4784283

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trans-2-Methyl-2-butenal

METLIN ID

Not Available

PubChem Compound

6028462

PDB ID

Not Available

ChEBI ID

88419

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1551461

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Tiglic aldehyde (HMDB0031512)

MOL for HMDB0031512 (Tiglic aldehyde)

3D MOL for HMDB0031512 (Tiglic aldehyde)

3D SDF for HMDB0031512 (Tiglic aldehyde)

3D-SDF for HMDB0031512 (Tiglic aldehyde)

PDB for HMDB0031512 (Tiglic aldehyde)

3D PDB for HMDB0031512 (Tiglic aldehyde)

SMILES for HMDB0031512 (Tiglic aldehyde)

INCHI for HMDB0031512 (Tiglic aldehyde)

Structure for HMDB0031512 (Tiglic aldehyde)

3D Structure for HMDB0031512 (Tiglic aldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra