Cannabis Compound Database: Showing Compound Card for (±)-trans-Linalyl oxide (CDB000294)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References XML

Read more...Show more...

Record Information

Version

1.0

Created at

2020-03-19 00:29:24 UTC

Updated at

2020-12-07 19:07:19 UTC

CannabisDB ID

CDB000294

Secondary Accession Numbers

Not Available

Cannabis Compound 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 SDF PDB SMILES InChI

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 Molecular Weight

170.25

Monoisotopic Molecular Weight

170.1307

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

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

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physical Properties

State

Solid

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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	(±)-trans-Linalyl oxide, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-e8c8defcb13d413ce23b	Spectrum
GC-MS	(±)-trans-Linalyl oxide, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-e8c8defcb13d413ce23b	Spectrum
Predicted GC-MS	(±)-trans-Linalyl oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9100000000-d76b0d8bd5839f5bad93	Spectrum
Predicted GC-MS	(±)-trans-Linalyl oxide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-003r-9720000000-d7880141bef77c136d15	Spectrum
Predicted GC-MS	(±)-trans-Linalyl oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-3717374e13c0e4e46e01	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fl0-7900000000-1a57b949dcbd663fc1eb	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbi-9000000000-29f24016ec67ee4e749b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-92d23807ba882368b9c5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-9591ca26dd3aa91ec77b	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00m0-9400000000-adb5d889f7dfc0e0d558	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-efbd93a1a83feefc94df	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-3900000000-6b8e798821e4115bf1d0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-ace0a44f890d3bb40734	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-8900000000-a536912550058a32831e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7p-9100000000-b3759eefd18d5faed102	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kc6-9000000000-369ce7815f6cf7814da3	2021-09-22	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0040727

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020535

KNApSAcK ID

C00034496

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

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]

Showing Compound Card for (±)-trans-Linalyl oxide (CDB000294)

Structure for CDB000294 ((±)-trans-Linalyl oxide)