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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:41 UTC

Update Date

2023-02-21 17:21:47 UTC

HMDB ID

HMDB0032242

Secondary Accession Numbers

HMDB32242

Metabolite Identification

Common Name

(E)-3,7-Dimethyl-1,5,7-octatrien-3-ol

Description

(E)-3,7-Dimethyl-1,5,7-octatrien-3-ol, also known as dehydro-linalool or 2,7-dimethyl-7-octen-5-yn-4-ol, belongs to the class of organic compounds known as ynones. These are organic compounds containing the ynone functional group, an alpha,beta unsaturated ketone group with the general structure RC#C-C(=O)R' (R' not H). Based on a literature review very few articles have been published on (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol.

Structure

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

COMPND    HMDB0032242
HETATM    1  C1  UNL     1       3.729   2.043   1.257  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.913   1.330   0.727  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.911   0.458   0.053  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.641  -0.709  -0.575  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.337   1.217  -0.983  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.901   0.001   1.058  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.157  -0.888   0.517  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.996  -0.310  -0.555  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.290  -0.170  -0.385  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.190   0.406  -1.424  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.930  -0.600   0.910  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.446   2.682   1.708  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.595  -0.345  -0.991  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.068  -1.166  -1.404  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.855  -1.508   0.186  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.770   0.981  -1.841  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.468  -0.592   1.834  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.441   0.872   1.588  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.831  -1.296   1.326  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.287  -1.834   0.076  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.527  -0.014  -1.475  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.619   1.021  -2.152  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.971   0.981  -0.901  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.624  -0.439  -2.005  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.991  -0.368   0.941  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.808  -1.700   1.003  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.428  -0.054   1.734  1.00  0.00           H  
CONECT    1    2    2    2   12
CONECT    2    3
CONECT    3    4    5    6
CONECT    4   13   14   15
CONECT    5   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9    9   21
CONECT    9   10   11
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,7-Dimethyl-7-octen-5-yn-4-ol	HMDB
3,7-Dimethyl-6-octen-1-yn-3-ol	HMDB
3,7-Dimethyloct-6-en-1-yn-3-ol	HMDB
Dehydro-linalool	HMDB
Linalool, dehydro- (6ci)	HMDB
Dehydrolinalool	HMDB
Dehydro-beta-linalool	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

3,7-dimethyloct-6-en-1-yn-3-ol

Traditional Name

3,7-dimethyloct-6-en-1-yn-3-ol

CAS Registry Number

29171-20-8

SMILES

CC(C)=CCCC(C)(O)C#C

InChI Identifier

InChI=1S/C10H16O/c1-5-10(4,11)8-6-7-9(2)3/h1,7,11H,6,8H2,2-4H3

InChI Key

YWTIDNZYLFTNQQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ynones. These are organic compounds containing the ynone functional group, an alpha,beta unsaturated ketone group with the general structure RC#C-C(=O)R' (R' not H).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ynones

Alternative Parents

Substituents

Ynone
Tertiary alcohol
Acetylide
Hydrocarbon derivative
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032242)
Cytoplasm (HMDB: HMDB0032242)

Source

Endogenous

Endogenous (HMDB: HMDB0032242)

Exogenous

Food

Food (HMDB: HMDB0032242)

Exogenous (HMDB: HMDB0032242)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-58.00 to -56.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	198.00 to 199.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1084 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.610	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	2.03	ALOGPS
logP	2.14	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	16	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.62 m³·mol⁻¹	ChemAxon
Polarizability	18.45 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]+	136.405	31661259
DarkChem	[M-H]-	134.147	31661259
DeepCCS	[M+H]+	136.887	30932474
DeepCCS	[M-H]-	133.243	30932474
DeepCCS	[M-2H]-	170.5	30932474
DeepCCS	[M+Na]+	145.756	30932474
AllCCS	[M+H]+	135.7	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	136.3	32859911
AllCCS	[M+HCOO]-	138.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.0 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7201 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2035.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	379.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	210.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	81.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	518.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	604.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1006.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	979.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	373.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	481.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-3,7-Dimethyl-1,5,7-octatrien-3-ol	CC(C)=CCCC(C)(O)C#C	1616.8	Standard polar	33892256
(E)-3,7-Dimethyl-1,5,7-octatrien-3-ol	CC(C)=CCCC(C)(O)C#C	1070.5	Standard non polar	33892256
(E)-3,7-Dimethyl-1,5,7-octatrien-3-ol	CC(C)=CCCC(C)(O)C#C	1087.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-3,7-Dimethyl-1,5,7-octatrien-3-ol,1TMS,isomer #1	C#CC(C)(CCC=C(C)C)O[Si](C)(C)C	1230.5	Semi standard non polar	33892256
(E)-3,7-Dimethyl-1,5,7-octatrien-3-ol,1TBDMS,isomer #1	C#CC(C)(CCC=C(C)C)O[Si](C)(C)C(C)(C)C	1454.1	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 - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-9100000000-d156f13f64bb328e1e6a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9310000000-69bc402e8dc310221973	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 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 - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 10V, Positive-QTOF	splash10-0udi-1900000000-a7447e3a4cb38dae5a93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 20V, Positive-QTOF	splash10-0gbi-9500000000-0800c095ee6bd5539131	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 40V, Positive-QTOF	splash10-0gb9-9000000000-b2b36f12a2841bd3ba5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 10V, Negative-QTOF	splash10-0udi-1900000000-5bc6fa487ac6fa65ac68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 20V, Negative-QTOF	splash10-0udi-4900000000-b2c786eeb4907ea2e526	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 40V, Negative-QTOF	splash10-014i-9400000000-e66b6c44cfd7c7c564bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 10V, Positive-QTOF	splash10-003r-9100000000-8d615647cb5afd64d046	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 20V, Positive-QTOF	splash10-0f9x-9000000000-3bd2b1f3d755f73f2cf6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 40V, Positive-QTOF	splash10-004i-9000000000-cc819860ca6c2a06c583	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 10V, Negative-QTOF	splash10-0udi-0900000000-4655e57718913c9d2ebb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 20V, Negative-QTOF	splash10-0udi-3900000000-11f8275fdccba9e8ccf9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol 40V, Negative-QTOF	splash10-0gb9-9100000000-58561e88ee766e5d7e8f	2021-09-23	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+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

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB009329

KNApSAcK ID

C00052475

Chemspider ID

56576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62842

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020411

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lapczynski A, Bhatia SP, Letizia CS, Api AM: Fragrance material review on dehydrolinalool. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S117-20. doi: 10.1016/j.fct.2008.06.036. Epub 2008 Jul 1. [PubMed:18640188 ]
Kline DL, Bernier UR, Posey KH, Barnard DR: Olfactometric evaluation of spatial repellents for Aedes aegypti. J Med Entomol. 2003 Jul;40(4):463-7. [PubMed:14680112 ]
(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for (E)-3,7-Dimethyl-1,5,7-octatrien-3-ol (HMDB0032242)

MOL for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

3D MOL for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

3D SDF for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

3D-SDF for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

PDB for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

3D PDB for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

SMILES for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

INCHI for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

Structure for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

3D Structure for HMDB0032242 ((E)-3,7-Dimethyl-1,5,7-octatrien-3-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra