NP-MRD: Showing NP-Card for (±)-cis-Linalyl oxide (NP0044985)

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Record Information

Version

2.0

Created at

2022-03-10 18:52:16 UTC

Updated at

2022-03-10 22:11:42 UTC

NP-MRD ID

NP0044985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-cis-Linalyl oxide

Description

(±)-Cis-Linalyl oxide, also known as cis-Linalool-oxide or Linalool oxide B, 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. Biochemically, cis-Linalool-oxide is a monoterpenoid as it synthesized via multiple isoprene units. 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 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. More specifically, cis-Linalool-oxide has a sweet, earthy, and floral aroma and is used as a perfuming agent and a flavoring agent. Cis-Linalool-oxide exists as a clear or slightly yellow oil. It is a neutral, hydrophobic molecule that is insoluble in water. Cis-Linalool-oxide is found in black and green tea leaves has also been detected, but not quantified in, several different foods, spices or oils, such as sweet basils, black elderberries, coriander, common oregano, garden tomato (var.), Peppermint oil and papaya. Cis-Linalool oxide is also found in Lavender (https://Doi.Org/10.4028/Www.Scientific.Net/KEM.688.31). Cis-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
    3.0091    1.7495    0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8011    0.4487    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -0.2208   -0.0452 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0727   -0.9456   -1.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147   -1.2494    0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3798   -0.9368    0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5250   -0.1512   -0.3254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8362    0.5570   -0.4050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9283   -0.5050   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284    1.4439    0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746    1.3138   -1.5518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5765    0.6599   -0.2953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132    2.3724   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832    2.1987    0.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054   -0.1592    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221   -0.3098   -2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1170   -1.3253   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -1.8685   -1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5854   -1.2072    1.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994   -2.2879    0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9892   -1.8501    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470   -0.3291    1.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -0.8515   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8617   -0.0300   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0459   -0.8730    0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6203   -1.3661   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2860    2.1038    1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0522    2.0137    0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722    0.8096    1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2831    0.7954   -2.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
  8 11  1  6
  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  6
  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                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -2.417   1.251   1.829  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.913  -0.016  -1.175  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.856   0.943   0.822  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.499  -1.252  -0.296  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.852   0.091   1.632  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.035   0.113  -1.506  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.131   0.729  -0.660  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.645  -0.786  -0.537  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.974  -0.273  -0.048  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.391  -0.399   0.303  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.529  -1.292   0.748  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.218  -1.085   0.482  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4   10                                                            
CONECT    5    1   10                                                       
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    6    9   12                                                  
CONECT    9    2    3    8   11                                             
CONECT   10    4    5    7   12                                             
CONECT   11    9                                                            
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₈O₂

Average Mass

170.2520 Da

Monoisotopic Mass

170.13068 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

11063-77-7

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-WPRPVWTQSA-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
Camellia sinensis	Plant	KNApSAcK
Cannabis sativa	NULL	Not Available
Citrus paradis	Plant	KNApSAcK
Citrus paradisi	Plant	KNApSAcK
Hesperis matronalis	Plant	KNApSAcK
Lonicera japonica	Plant	KNApSAcK
Myrtus communis	LOTUS Database	35616633
Osmanthus fragrans	Plant	KNApSAcK
Pelargonium graveolens	Plant	KNApSAcK
Rhaphiolepis bibas	Plant	KNApSAcK
Senegalia berlandieri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxolanes

Sub Class

Not Available

Direct Parent

Oxolanes

Alternative Parents

Substituents

Tertiary alcohol
Oxolane
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	19.47 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11116492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (±)-cis-Linalyl oxide (NP0044985)

MOL for NP0044985 ((±)-cis-Linalyl oxide)

3D MOL for NP0044985 ((±)-cis-Linalyl oxide)

3D SDF for NP0044985 ((±)-cis-Linalyl oxide)

3D-SDF for NP0044985 ((±)-cis-Linalyl oxide)

PDB for NP0044985 ((±)-cis-Linalyl oxide)

3D PDB for NP0044985 ((±)-cis-Linalyl oxide)

SMILES for NP0044985 ((±)-cis-Linalyl oxide)

INCHI for NP0044985 ((±)-cis-Linalyl oxide)

Structure for NP0044985 ((±)-cis-Linalyl oxide)

3D Structure for NP0044985 ((±)-cis-Linalyl oxide)