NP-MRD: Showing NP-Card for (±)-trans-Linalyl oxide (NP0044986)

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Record Information

Version

2.0

Created at

2022-03-10 18:52:17 UTC

Updated at

2022-03-10 22:11:43 UTC

NP-MRD ID

NP0044986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-trans-Linalyl oxide

Description

(±)-Trans-Linalyl oxide, also known as (E)-linalool oxide or trans-Linalool oxide is an oxidized derivative of Linalool which is a terpene alcohol common in various flowers and spice plants. It belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. From a biosynthetic point of view, trans-Linalool oxide is a monoterpenoid. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Linalool oxide occurs in two distinctly different structural guises in nature. The most common structural form is based on a five member, furan-like ring structure. The less common form is based on a six member, pyran-like structure. Both types of linalool oxide exist as cis- and trans- isomers. Despite the differences in structure, the aromas of the different forms of linalool oxide have a strong family resemblance. The furan-based linalool oxide has a floral character, somewhat reminiscent of lavender, but this is dominated by the profile of black tea. The pyran-based linalool oxide is more obviously floral, with less resemblance to tea. It is used as a perfuming agent and a flavoring agent. Trans-Linalool oxide exists as a clear or slightly yellow oil. It is a neutral, hydrophobic molecule that is insoluble in water. (±)-Trans-Linalyl oxide is found within tea and ceylon cinnamons and has also been detected, but not quantified in, several different foods, such as common oregano, sweet basils, garden tomatoes, gingers, and tarragons. Trans-Linalool oxide is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645 ) And the combination of these terpenoids produces the skunky, fruity odor characteristic of C. Savita

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -3.2706    0.5653    0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1643    0.9125    0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -0.1005   -0.7263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1228   -0.3929   -2.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2522   -1.3968    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2287   -1.4090    0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5379    0.0699    0.2531 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0131    0.3406    0.1498 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6921   -0.4522   -0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043    1.7997   -0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5787   -0.0312    1.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1355    0.4088   -0.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6173   -0.4581    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    1.2707    1.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384    1.9426    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -1.0956   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929    0.5193   -2.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902   -0.8670   -2.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847   -1.3250    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -2.2786   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7422   -1.9902   -0.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4188   -1.8097    1.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    0.5447    1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8713   -1.5024   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7199   -0.0082   -1.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2126   -0.3883   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554    1.9575   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4768    2.4317    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    2.0362    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3447    0.7061    2.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
  8 11  1  1
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3 12  1  0
  3  2  1  1
  2  1  2  3
 12  7  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
  7 23  1  1
  6 21  1  0
  6 22  1  0
  5 19  1  0
  5 20  1  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  2 15  1  0
  1 13  1  0
  1 14  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  O   UNK     0       0.770   1.090   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.476   0.185   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -1.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540  -1.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.016   0.185   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.481   0.661   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.801   2.167   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.625  -0.370   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.945   1.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.941   0.661   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.717   1.706   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.085  -0.370   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   10   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    2   12                                                       
CONECT   11    2                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
(e)-Linalool oxide a	HMDB
5-Ethenyltetrahydro-a,a,5-trimethyl-(2R,5R)-rel-2-furanmethanol	HMDB
e-Linalool oxide (furanoid)	HMDB
Linalool oxide a	HMDB
Linalool oxide II	HMDB
trans-Furanoid linalool oxide	HMDB
trans-Linalool 3,6-oxide	HMDB
trans-Linalool oxide (furanoid)	HMDB

Chemical Formula

C₁₀H₁₈O₂

Average Mass

170.2487 Da

Monoisotopic Mass

170.13068 Da

IUPAC Name

2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol

Traditional Name

2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol

CAS Registry Number

34995-77-2

SMILES

CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C

InChI Identifier

InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1

InChI Key

BRHDDEIRQPDPMG-WCBMZHEXSA-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
Artemisia dracunculus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cannabis sativa	NULL	Not Available
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus iyo	LOTUS Database	35616633
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hesperis matronalis	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vachellia rigidula	LOTUS Database	35616633
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Tertiary alcohol
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	1.51	ALOGPS
logP	1.67	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.04 m³·mol⁻¹	ChemAxon
Polarizability	19.52 Å³	ChemAxon
Number of Rings	1	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

HMDB0040727

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020535

KNApSAcK ID

Not Available

Chemspider ID

4937513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6432254

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (±)-trans-Linalyl oxide (NP0044986)

MOL for NP0044986 ((±)-trans-Linalyl oxide)

3D MOL for NP0044986 ((±)-trans-Linalyl oxide)

3D SDF for NP0044986 ((±)-trans-Linalyl oxide)

3D-SDF for NP0044986 ((±)-trans-Linalyl oxide)

PDB for NP0044986 ((±)-trans-Linalyl oxide)

3D PDB for NP0044986 ((±)-trans-Linalyl oxide)

SMILES for NP0044986 ((±)-trans-Linalyl oxide)

INCHI for NP0044986 ((±)-trans-Linalyl oxide)

Structure for NP0044986 ((±)-trans-Linalyl oxide)

3D Structure for NP0044986 ((±)-trans-Linalyl oxide)