NP-MRD: Showing NP-Card for Laurylaldehyde (NP0044912)

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Record Information

Version

2.0

Created at

2022-03-10 18:50:59 UTC

Updated at

2022-03-10 22:21:31 UTC

NP-MRD ID

NP0044912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Laurylaldehyde

Description

Laurylaldehyde also known as lauric aldehyde, belongs to the class of organic compounds known as medium-chain aldehydes, with a chain length between 6 and 12 carbon atoms. It has a dodecane backbone where the two hydrogens attached to a terminal carbon are replaced by an oxo group. Lauric aldehyde is a fatty aldehyde lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. It is a colorless to pale yellow clear liquid with an aldehydic, green, floral citrus, soapy, and waxy odor with a soapy, waxy, citrus, orange, mandarin flavor ( http://Www.Thegoodscentscompany.Com/data/rw1000371.Html#toorgano). Lauryl aldehyde is found in highest concentrations in corianders, sweet oranges, and lemons and in lower concentrations in mandarin orange (clementine, tangerine) and limes. Lauryl aldehyde has also been detected in fruits, mollusks, citrus, carrots, and wild celeries. This could make lauryl aldehyde a potential biomarker for the consumption of these foods. Lauryl aldehyde was found in cannabis plants (PMID:6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
   -4.5115    2.0644   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.5761    0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8836    0.2994    0.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6153   -1.1375    0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1319   -1.3762    0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4419   -1.0039   -0.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -1.2934   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6697   -0.5211    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1319   -0.8226    0.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8117   -0.4550   -0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6189    1.0290   -0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1933    1.8364    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6367    2.0550    1.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212    2.2553   -1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5363    2.4289    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8619    2.6541    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9003    0.2734    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7995    0.0063   -0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384    0.6908   -0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134    0.9092    1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1191   -1.4052    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0756   -1.7986   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7532   -0.7051    1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002   -2.4026    1.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5759    0.0955   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141   -1.5917   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4971   -0.9924   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1213   -2.4036   -0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4187    0.5487    0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962   -0.7665    1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -1.9051    1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5693   -0.2624    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849   -1.0895   -1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9173   -0.6774   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1134    1.3084   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675    1.3135   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1773    2.2656    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      26.221   7.438   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
Dodecanaldehyde	ChEBI
Dodecyl aldehyde	ChEBI
Lauryl aldehyde	ChEBI
Laurylaldehyde	ChEBI
N-Dodecanal	ChEBI
N-Dodecyl aldehyde	ChEBI
N-Dodecylic aldehyde	ChEBI
N-Lauraldehyde	ChEBI
Dodecanal	Kegg
Lauraldehyde	Kegg
1-Dodecanal	HMDB
1-Dodecyl aldehyde	HMDB
Aldehyde C-12, lauric	HMDB
Aldehyde C12	HMDB
C-12 Aldehyde, lauric	HMDB
C-12 Lauric aldehyde	HMDB
C12 Aldehyde	HMDB
Dodecylaldehyde	HMDB
Duodecylic aldehyde	HMDB
FEMA 2615	HMDB
Lauraldehyde (8ci)	HMDB
Laurinaldehyde	HMDB
Lauric aldehyde	ChEBI

Chemical Formula

C₁₂H₂₄O

Average Mass

184.3184 Da

Monoisotopic Mass

184.18272 Da

IUPAC Name

dodecanal

Traditional Name

dodecanal

CAS Registry Number

112-54-9

SMILES

CCCCCCCCCCCC=O

InChI Identifier

InChI=1S/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h12H,2-11H2,1H3

InChI Key

HFJRKMMYBMWEAD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Aspalathus linearis	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Citrus aurantiifolia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus iyo	LOTUS Database	35616633
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus spp.	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clinopodium gilliesii	LOTUS Database	35616633
Coriandrum sativum	LOTUS Database	35616633
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota	LOTUS Database	35616633
Daucus carota ssp. sativus	FooDB	David M. Alabran, Howard R. Moskowitz, and Ahmed F. Mabrouk. Carrot-Root Oil Components and Their...
Eruca vesicaria subsp. Sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Eryngium foetidum	LOTUS Database	35616633
Etlingera elatior	LOTUS Database	35616633
Gymnodinium nagasakiense	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Houttuynia cordata	Plant	KNApSAcK
Houttuynia emeiensis	Plant	KNApSAcK
Ligusticum sinense	LOTUS Database	35616633
Machilus bombycina	Plant	KNApSAcK
Mikania cordifolia	LOTUS Database	35616633
Petasites albus	Plant	KNApSAcK
Petasites hybridus	Plant	KNApSAcK
Phagnalon sordidum	Plant	KNApSAcK
Polygonum minus	Plant	KNApSAcK
Prunus avium	Plant	KNApSAcK
Ruta graveolens	LOTUS Database	35616633
Scytosiphon lomentaria	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633
Vaccinium macrocarpon	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty aldehyde (CHEBI:27836 )
2,3-saturated fatty aldehyde (CHEBI:27836 )
Fatty aldehydes (C02278 )
Fatty aldehydes (LMFA06000071 )
a fatty aldehyde (CPD-7880 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.46	ALOGPS
logP	4.32	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-6.9	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	10	ChemAxon
Refractivity	57.75 m³·mol⁻¹	ChemAxon
Polarizability	24.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033933

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Dodecanal

METLIN ID

Not Available

PubChem Compound

8194

PDB ID

Not Available

ChEBI ID

27836

Good Scents ID

Not Available

References

General References

Ambily PS, Jisha MS: Metabolic profile of sodium dodecyl sulphate (SDS) biodegradation by Pseudomonas aeruginosa (MTCC 10311). J Environ Biol. 2014 Sep;35(5):827-31. [PubMed:25204054 ]
Donega MA, Mello SC, Moraes RM, Jain SK, Tekwani BL, Cantrell CL: Pharmacological activities of cilantro's aliphatic aldehydes against Leishmania donovani. Planta Med. 2014 Dec;80(18):1706-11. doi: 10.1055/s-0034-1383183. Epub 2014 Oct 23. [PubMed:25340465 ]
Ahmad R, Baharum SN, Bunawan H, Lee M, Mohd Noor N, Rohani ER, Ilias N, Zin NM: Volatile profiling of aromatic traditional medicinal plant, Polygonum minus in different tissues and its biological activities. Molecules. 2014 Nov 20;19(11):19220-42. doi: 10.3390/molecules191119220. [PubMed:25420073 ]
Sekhon JK, Maness NO, Jones CL: Effect of preprocessing and compressed propane extraction on quality of cilantro (Coriandrum sativum L.). Food Chem. 2015 May 15;175:322-8. doi: 10.1016/j.foodchem.2014.11.153. Epub 2014 Dec 3. [PubMed:25577087 ]

Showing NP-Card for Laurylaldehyde (NP0044912)

MOL for NP0044912 (Laurylaldehyde)

3D MOL for NP0044912 (Laurylaldehyde)

3D SDF for NP0044912 (Laurylaldehyde)

3D-SDF for NP0044912 (Laurylaldehyde)

PDB for NP0044912 (Laurylaldehyde)

3D PDB for NP0044912 (Laurylaldehyde)

SMILES for NP0044912 (Laurylaldehyde)

INCHI for NP0044912 (Laurylaldehyde)

Structure for NP0044912 (Laurylaldehyde)

3D Structure for NP0044912 (Laurylaldehyde)