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Showing NP-Card for trans-Rose oxide (NP0046813)

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Record Information
Version2.0
Created at2022-03-17 20:29:56 UTC
Updated at2022-03-17 20:29:57 UTC
NP-MRD IDNP0046813
Secondary Accession NumbersNone
Natural Product Identification
Common Nametrans-Rose oxide
DescriptionRose oxide, also known as fema 3236 or rose oxide levo, belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Rose oxide can be produced industrially beginning with photooxygenation of citronellol to give the allyl hydroperoxide which is then reduced with sodium sulfite to provide the diol. Rose oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Rose oxide is an organic compound of the pyran class of monoterpenes. Rose oxide is a fresh, geranium, and green tasting compound. Outside of the human body, Rose oxide is found, on average, in the highest concentration within lemon balms and peppermints. Rose oxide has also been detected, but not quantified in, a few different foods, such as black elderberries, cucumbers, and gingers. This could make rose oxide a potential biomarker for the consumption of these foods. It also contributes to the flavor of some fruits, such as lychee, and wines, such as Gewürztraminer. Ring-closure with sulfuric acid forms both the cis- and trans-isomers in equal amounts. Rose oxide is a fragrance chemical found in roses and rose oil. trans-Rose oxide is found in Aloysia triphylla, Citrus limon, Corymbia citriodora, Cryptomeria japonica, Daphne odora, Magnolia kobus, Paeonia lactiflora, Pelargonium graveolens, Pelargonium quercifolium, Pelargonium vitifolium, Pimenta racemosa, Rosa centifolia, Rosa damascena and Swertia japonica. trans-Rose oxide was first documented in 1999 (PMID: 10564036). The compound has a cis- and a trans-isomer, each with a (+)- and (−)-stereoisomer, but only the (−)-cis isomer (odor threshold 0.5 Ppb) is responsible for the typical rose (floral green) fragrance (PMID: 18247534) (PMID: 23122727) (PMID: 24518327) (PMID: 25212332) (PMID: 25911965) (PMID: 26126958).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046813 (trans-Rose oxide)


  Mrv0541 05061308532D          

 11 11  0  0  0  0            999 V2000
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
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3D MOL for NP0046813 (trans-Rose oxide)

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3D SDF for NP0046813 (trans-Rose oxide)

  Mrv0541 05061308532D          

 11 11  0  0  0  0            999 V2000
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCOC(C1)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3

> <INCHI_KEY>
CZCBTSFUTPZVKJ-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.33411672481161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methyl-2-(2-methylprop-1-en-1-yl)oxane

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
2.6829478226666668

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.172092453567934

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
48.49150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rose oxide

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046813 (trans-Rose oxide)
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PDB for NP0046813 (trans-Rose oxide)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    8   10                                                       
CONECT    7    9   10                                                       
CONECT    8    1    2    6                                                  
CONECT    9    3    4    7                                                  
CONECT   10    6    7   11                                                  
CONECT   11    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0046813 (trans-Rose oxide)
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SMILES for NP0046813 (trans-Rose oxide)
CC1CCOC(C1)C=C(C)C
Download
INCHI for NP0046813 (trans-Rose oxide)
InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3
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Synonyms
ValueSource
4-Methyl-2-(2-methyl-1-propenyl)tetrahydro-2H-pyranChEBI
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyranChEBI
Tetrahydro-4-methyl-2-(2-methylprop-1-enyl)pyranChEBI
(Z)-Rose oxideHMDB
2-Isobutenyl-4-methyltetrahydropyranHMDB
cis Rose oxideHMDB
FEMA 3236HMDB
Rose oxide , IHMDB
Rose oxide cisHMDB
Rose oxide levoHMDB
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)pyran, 9ciHMDB
Tetrahydro-4-methyl-2-[2-methyl-1-propenyl]-2H-pyranHMDB
Rose-oxideHMDB
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name4-methyl-2-(2-methylprop-1-en-1-yl)oxane
Traditional Namerose oxide
CAS Registry Number5542-69-8
SMILES
CC1CCOC(C1)C=C(C)C
InChI Identifier
InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3
InChI KeyCZCBTSFUTPZVKJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloysia triphyllaLOTUS Database
Citrus limonLOTUS Database
Corymbia citriodoraLOTUS Database
Cryptomeria japonicaLOTUS Database
Cucumis sativus L.FooDB
    • Ancheng Zhou and Roger F. McFeeters. Volatile Compounds in Cucumbers Fermented in Low-Salt Condit...
Daphne odoraLOTUS Database
Magnolia kobusLOTUS Database
Melissa officinalis L.FooDB
Mentha x piperitaFooDB
Paeonia lactifloraLOTUS Database
Pelargonium graveolensLOTUS Database
Pelargonium quercifoliumLOTUS Database
Pelargonium vitifoliumLOTUS Database
Pimenta racemosaLOTUS Database
Rosa centifoliaLOTUS Database
Rosa damascenaLOTUS Database
Sambucus nigraFooDB
Swertia japonicaLOTUS Database
VitisFooDB
Zingiber officinaleFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassOxanes  
Sub ClassNot Available
Direct ParentOxanes  
Alternative Parents
Substituents
  • Oxane
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.3ALOGPS
logP2.68ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.49 m³·mol⁻¹ChemAxon
Polarizability19.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036097  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014937  
KNApSAcK IDNot Available
Chemspider ID25927  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRose_oxide  
METLIN IDNot Available
PubChem Compound27866  
PDB IDNot Available
ChEBI ID90075  
Good Scents IDNot Available
References
General References
  1. Wust M, Beck T, Mosandl A: Conversion of citronellyl diphosphate and citronellyl beta-D-glucoside into rose oxide by Pelargonium graveolens. J Agric Food Chem. 1999 Apr;47(4):1668-72. doi: 10.1021/jf980972e. [PubMed:10564036  ] 
  2. Koslitz S, Renaud L, Kohler M, Wust M: Stereoselective formation of the varietal aroma compound rose oxide during alcoholic fermentation. J Agric Food Chem. 2008 Feb 27;56(4):1371-5. doi: 10.1021/jf072518t. Epub 2008 Feb 2. [PubMed:18247534  ] 
  3. Nonato FR, Santana DG, de Melo FM, dos Santos GG, Brustolim D, Camargo EA, de Sousa DP, Soares MB, Villarreal CF: Anti-inflammatory properties of rose oxide. Int Immunopharmacol. 2012 Dec;14(4):779-84. doi: 10.1016/j.intimp.2012.10.015. Epub 2012 Nov 1. [PubMed:23122727  ] 
  4. Ruiz-Garcia L, Hellin P, Flores P, Fenoll J: Prediction of Muscat aroma in table grape by analysis of rose oxide. Food Chem. 2014 Jul 1;154:151-7. doi: 10.1016/j.foodchem.2014.01.005. Epub 2014 Jan 10. [PubMed:24518327  ] 
  5. Piantini U, Schrader J, Wawrzun A, Wust M: A biocatalytic route towards rose oxide using chloroperoxidase. Food Chem. 2011 Dec 1;129(3):1025-9. doi: 10.1016/j.foodchem.2011.05.068. Epub 2011 May 25. [PubMed:25212332  ] 
  6. Song M, Xia Y, Tomasino E: Investigation of a Quantitative Method for the Analysis of Chiral Monoterpenes in White Wine by HS-SPME-MDGC-MS of Different Wine Matrices. Molecules. 2015 Apr 22;20(4):7359-78. doi: 10.3390/molecules20047359. [PubMed:25911965  ] 
  7. Nakahashi H, Yamamura Y, Usami A, Rangsunvigit P, Malakul P, Miyazawa M: Metabolism of (-)-cis- and (-)-trans-rose oxide by cytochrome P450 enzymes in human liver microsomes. Biopharm Drug Dispos. 2015 Dec;36(9):565-74. doi: 10.1002/bdd.1965. Epub 2015 Oct 31. [PubMed:26126958  ]