NP-MRD: Showing NP-Card for (2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal (NP0220193)

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Record Information

Version

2.0

Created at

2022-09-05 21:25:54 UTC

Updated at

2022-09-05 21:25:54 UTC

NP-MRD ID

NP0220193

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal

Description

(4E,6E)-dehydromanoalide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal is found in Luffariella variabilis. (2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal was first documented in 2015 (PMID: 26197501). Based on a literature review very few articles have been published on (4E,6E)-dehydromanoalide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223252D          

 29 30  0  0  1  0            999 V2000
  -12.1460    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0483    1.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3033    0.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183    0.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283    0.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3832    1.7437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1678    1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6191    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1494    1.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    1.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END


  Mrv1652309052223252D          

 29 30  0  0  1  0            999 V2000
  -12.1460    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0483    1.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3033    0.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183    0.2916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283    0.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3832    1.7437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1678    1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6191    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1494    1.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    1.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    3.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220193

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CCC1=C(C)CCCC1(C)C)=C/CC\C(C=O)=C/C=C/C1=CC(=O)O[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O4/c1-18(13-14-22-19(2)9-7-15-25(22,3)4)8-5-10-20(17-26)11-6-12-21-16-23(27)29-24(21)28/h6,8,11-12,16-17,24,28H,5,7,9-10,13-15H2,1-4H3/b12-6+,18-8+,20-11+/t24-/m1/s1

> <INCHI_KEY>
CNZFPEKVGJSRBD-DBNLUOHASA-N

> <FORMULA>
C25H34O4

> <MOLECULAR_WEIGHT>
398.543

> <EXACT_MASS>
398.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.926082112214175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,5E)-2-[(2E)-3-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal

> <JCHEM_LOGP>
5.321889349000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.774424010020649

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.337506562676798

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2833381817940195

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
120.58099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,5E)-2-[(2E)-3-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -22.673   8.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -22.673   6.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -21.339   5.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -20.005   6.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -20.005   8.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.672   8.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -18.672  10.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -17.338   8.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.004   8.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.670   8.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.337   8.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.337  10.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -12.003  11.090   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -12.003   8.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003   6.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669   5.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669   4.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.424   3.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.899   1.790   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.994   0.544   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -11.439   1.790   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -11.915   3.255   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -13.380   3.731   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -21.339   4.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -19.822   4.427   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -20.812   2.713   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -22.673   3.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -24.006   4.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -24.006   5.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24    3   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    2                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₄

Average Mass

398.5430 Da

Monoisotopic Mass

398.24571 Da

IUPAC Name

(2E,5E)-2-[(2E)-3-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal

Traditional Name

(2E,5E)-2-[(2E)-3-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal

CAS Registry Number

Not Available

SMILES

C\C(CCC1=C(C)CCCC1(C)C)=C/CC\C(C=O)=C/C=C/C1=CC(=O)O[C@H]1O

InChI Identifier

InChI=1S/C25H34O4/c1-18(13-14-22-19(2)9-7-15-25(22,3)4)8-5-10-20(17-26)11-6-12-21-16-23(27)29-24(21)28/h6,8,11-12,16-17,24,28H,5,7,9-10,13-15H2,1-4H3/b12-6+,18-8+,20-11+/t24-/m1/s1

InChI Key

CNZFPEKVGJSRBD-DBNLUOHASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Luffariella variabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
2-furanone
Alpha,beta-unsaturated aldehyde
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enal
Carboxylic acid ester
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Aldehyde
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	5.32	ChemAxon
pKa (Strongest Acidic)	7.34	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	120.58 m³·mol⁻¹	ChemAxon
Polarizability	45.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24700134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575952

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hamada T, Harada D, Hirata M, Yamashita K, Palaniveloo K, Okamura H, Iwagawa T, Arima N, Iriguchi T, de Voogd NJ, Vairappan CS: Manoalide-related Sesterterpene from the Marine Sponge Luffariella variabilis. Nat Prod Commun. 2015 Jun;10(6):863-4. [PubMed:26197501 ]
LOTUS database [Link]

Showing NP-Card for (2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal (NP0220193)

MOL for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

3D MOL for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

3D SDF for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

3D-SDF for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

PDB for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

3D PDB for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

SMILES for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

INCHI for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

Structure for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)

3D Structure for NP0220193 ((2e,5e)-2-[(2e)-3-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]prop-2-en-1-ylidene]-6-methyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)oct-5-enal)