Hmdb loader

Showing metabocard for Benzaldehyde (HMDB0006115)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-24 13:52:54 UTC
Update Date2023-02-21 17:17:14 UTC
HMDB IDHMDB0006115
Secondary Accession Numbers
  • HMDB06115
Metabolite Identification
Common NameBenzaldehyde
DescriptionBenzaldehyde is occasionally found as a volatile component of urine. Benzaldehyde is an aromatic aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance. Currently used in only seven cosmetic products, its highest reported concentration of use was 0.5% in perfumes. Benzaldehyde is a generally regarded as safe (GRAS) food additive in the United States and is accepted as a flavoring substance in the European Union. Because Benzaldehyde rapidly metabolizes to Benzoic Acid in the skin, the available dermal irritation and sensitization data demonstrating no adverse reactions to Benzoic Acid were considered supportive of the safety of Benzaldehyde. Benzaldehyde is absorbed through skin and by the lungs, distributes to all well-perfused organs, but does not accumulate in any specific tissue type. After being metabolized to benzoic acid, conjugates are formed with glycine or glucuronic acid, and excreted in the urine. Several studies have suggested that Benzaldehyde can have carcinostatic or antitumor properties. Overall, at the concentrations used in cosmetics, Benzaldehyde was not considered a carcinogenic risk to humans. Although there are limited irritation and sensitization data available for Benzaldehyde, the available dermal irritation and sensitization data and ultraviolet (UV) absorption and phototoxicity data demonstrating no adverse reactions to Benzoic Acid support the safety of Benzaldehyde as currently used in cosmetic products. (PMID:16835129 , Int J Toxicol. 2006;25 Suppl 1:11-27.).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006115 (Benzaldehyde)

  Mrv1652309272007442D          

  8  8  0  0  0  0            999 V2000
    0.5802    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0006115 (Benzaldehyde)

HMDB0006115
     RDKit          3D
Benzaldehyde
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.9385    1.1037   -0.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    0.0556    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436   -0.0088    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1721    1.1857   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044    1.1292   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890   -0.0380   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155   -1.2080    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -1.1803    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8195   -0.8763    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    2.0760   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7284    2.0633   -0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.0496   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182   -2.1510    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7263   -2.1016    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  2  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
M  END
Download

3D SDF for HMDB0006115 (Benzaldehyde)

  Mrv1652309272007442D          

  8  8  0  0  0  0            999 V2000
    0.5802    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.5171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006115

> <DATABASE_NAME>
hmdb

> <SMILES>
O=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

> <INCHI_KEY>
HUMNYLRZRPPJDN-UHFFFAOYSA-N

> <FORMULA>
C7H6O

> <MOLECULAR_WEIGHT>
106.1219

> <EXACT_MASS>
106.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
11.01681252528575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzaldehyde

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
1.6857481606666664

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.111326959702501

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
32.641999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0006115 (Benzaldehyde)

HMDB0006115
     RDKit          3D
Benzaldehyde
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.9385    1.1037   -0.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    0.0556    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436   -0.0088    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1721    1.1857   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044    1.1292   -0.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890   -0.0380   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155   -1.2080    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -1.1803    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8195   -0.8763    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7355    2.0760   -0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7284    2.0633   -0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.0496   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182   -2.1510    0.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7263   -2.1016    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  2  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
M  END
Download

PDB for HMDB0006115 (Benzaldehyde)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.292   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.750   3.602   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.084   2.832   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
Download

3D PDB for HMDB0006115 (Benzaldehyde)

COMPND    HMDB0006115
HETATM    1  O1  UNL     1       2.938   1.104  -0.225  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.315   0.056   0.008  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.844  -0.009   0.010  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.172   1.186  -0.269  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.204   1.129  -0.269  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.889  -0.038  -0.008  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.216  -1.208   0.265  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.164  -1.180   0.271  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.819  -0.876   0.225  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.735   2.076  -0.467  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.728   2.063  -0.486  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.959  -0.050  -0.015  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.718  -2.151   0.475  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.726  -2.102   0.486  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    9
CONECT    3    4    4    8
CONECT    4    5   10
CONECT    5    6    6   11
CONECT    6    7   12
CONECT    7    8    8   13
CONECT    8   14
END
Download

SMILES for HMDB0006115 (Benzaldehyde)

O=CC1=CC=CC=C1
Download

INCHI for HMDB0006115 (Benzaldehyde)

InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H6O
Average Molecular Weight106.1219
Monoisotopic Molecular Weight106.041864814
IUPAC Namebenzaldehyde
Traditional Namebenzaldehyde
CAS Registry Number100-52-7
SMILES
O=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
InChI KeyHUMNYLRZRPPJDN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct ParentBenzoyl derivatives
Alternative Parents
Substituents
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-26 °CNot Available
Boiling Point62.00 to 63.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility6.95 mg/mL at 25 °CNot Available
LogP1.48HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014661
KNApSAcK IDC00034452
Chemspider ID235
KEGG Compound IDC00261
BioCyc IDBENZALDEHYDE
BiGG IDNot Available
Wikipedia LinkBenzaldehyde
METLIN IDNot Available
PubChem Compound240
PDB IDNot Available
ChEBI ID17169
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001491
References
Synthesis ReferenceOxidation products of aromatic hydrocarbons with methyl groups, substituting methyl groups or their derivatives. (1903), DE 175295 19030730 CAN 1:4512 AN 1907:4512
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Andersen A: Final report on the safety assessment of benzaldehyde. Int J Toxicol. 2006;25 Suppl 1:11-27. [PubMed:16835129 ]

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase family 8 member A1
General function:
Involved in oxidoreductase activity
Specific function:
Converts 9-cis-retinal to 9-cis-retinoic acid. Has lower activity towards 13-cis-retinal. Has much lower activity towards all-trans-retinal. Has highest activity with benzaldehyde and decanal (in vitro). Has a preference for NAD, but shows considerable activity with NADP (in vitro)
Gene Name:
ALDH8A1
Uniprot ID:
Q9H2A2
Molecular weight:
53400.9