Np mrd loader

Record Information
Version1.0
Created at2022-09-06 06:17:06 UTC
Updated at2022-09-06 06:17:06 UTC
NP-MRD IDNP0227062
Secondary Accession NumbersNone
Natural Product Identification
Common Nameβ phellandrene
DescriptionBeta-Phellandrene, also known as β-phellandren or 2-p-menthadiene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Beta-Phellandrene is possibly neutral. Beta-Phellandrene is a mint and terpentine tasting compound. Outside of the human body, beta-Phellandrene is found, on average, in the highest concentration within a few different foods, such as gingers, parsley, and dills and in a lower concentration in hyssops, lemons, and corianders. Beta-Phellandrene has also been detected, but not quantified in, several different foods, such as parsnips, pine nuts, ceylon cinnamons, celery stalks, and tarragons. This could make beta-phellandrene a potential biomarker for the consumption of these foods. One of a pair of phellandrene cyclic monoterpene double-bond isomers in which one double bond is exocyclic (cf. β phellandrene is found in Abies alba, Abies balsamea, Abies magnifica, Abies nordmanniana, Abies sachalinensis, Abies sibirica, Achillea nobilis, Agathosma betulina, Ageratum conyzoides, Aloysia citrodora, Anethum graveolens, Angelica archangelica, Angelica dahurica, Artemisia santonicum, Aspergillus candidus, Aster scaber, Atalantia buxifolia, Athamanta macedonica, Aucoumea klaineana, Austrobaileya scandens, Bellis perennis, Boronia latipinna, Bothriochloa bladhii, Brassica nigra, Bunium persicum, Bupleurum fruticosum, Callistemon linearis, Cannabis sativa, Cantinoa mutabilis, Catha edulis, Chamaecyparis obtusa, Chamaecyparis pisifera, Citrus aurantium, Citrus junos, Citrus limon, Citrus medica, Citrus natsudaidai, Citrus sinensis, Cleistopholis patens, Clinopodium carolinianum, Coriandrum sativum, Cotinus coggygria, Crithmum maritimum, Cryptomeria japonica, Cuminum cyminum, Cymbopogon flexuosus, Dacrydium nausoriense, Echinophora tenuifolia, Entandrophragma cylindricum, Coespeletia timotensis, Etlingera elatior, Eucalyptus apodophylla, Eucalyptus camaldulensis, Eucalyptus cloeziana, Eucalyptus cneorifolia, Eucalyptus cunninghamii, Eucalyptus delegatensis, Eucalyptus dolichorhyncha, Eucalyptus porosa, Eucalyptus punctata, Eugenia dysenterica, Ferula assa-foetida, Ferulago nodosa, Ferulago trachycarpa, Foeniculum vulgare, Gossypium hirsutum, Gossypium sturtianum, Helichrysum taenari, Heracleum dissectum, Heracleum persicum, Heterotheca subaxillaris, Hyssopus officinalis, Juniperus communis, Juniperus drupacea, Juniperus excelsa, Juniperus jaliscana, Juniperus monticola, Lantana camara, Larix gmelinii, Larix gmelinii, Larix kaempferi, Larix occidentalis, Larix sibirica, Laser trilobum, Laurus nobilis, Lavandula stoechas, Lepechinia chamaedryoides, Lepechinia urbanii, Levisticum officinale, Ligusticum porteri, Ligusticum sinense, Lindera neesiana, Lippia rehmannii, Liquidambar styraciflua, Liriodendron tulipifera, Machilus japonica, Magnolia balansae, Mangifera indica, Melaleuca alternifolia, Mentha aquatica, Mentha piperita, Mentha rotundifolia, Micromeria maderensis, Micromeria teneriffae, Molopospermum peloponnesiacum, Myrtus communis, Nasutitermes ephratae, Ocimum americanum, Oenanthe aquatica, Origanum acutidens, Origanum hypericifolium, Origanum laevigatum, Origanum onites, Origanum syriacum, Origanum vulgare, Parthenium confertum, Pelargonium endlicherianum, Pelargonium graveolens, Pelargonium quercifolium, Pelargonium vitifolium, Petroselinum crispum, Picea abies, Picea glehnii, Picea koraiensis, Picea schrenkiana, Picea sitchensis, Pimenta racemosa, Pinus brutia, Pinus densiflora, Pinus discolor, Pinus elliottii, Pinus flexilis, Pinus merkusii, Pinus monticola, Pinus pumila, Pinus rzedowskii, Pinus sylvestris, Piper auritum, Piper fimbriulatum, Piper guineense, Piper regnellii, Pistacia integerrima, Pistacia vera, Pittosporum balfourii, Plagiochila rutilans, Prangos uechtritzii, Quercus ilex, Renealmia alpinia, Rhanterium epapposum, Rhodiola rosea, Salvia aurea, Salvia columbariae, Salvia syriaca, Santiria trimera, Santolina chamaecyparissus, Santolina rosmarinifolia, Satureja cuneifolia, Satureja hortensis, Satureja spicigera, Scalesia aspera, Schinus molle, Sequoia sempervirens, Sequoiadendron giganteum, Sideritis leucantha, Sideritis tragoriganum, Skimmia laureola, Solidago odora, Stachys glutinosa, Steganotaenia araliacea, Stoebe vulgaris, Syzygium aromaticum, Tagetes minuta, Tanacetum millefolium, Tanacetum parthenium, Tanacetum vulgare, Targionia hypophylla, Teucrium cyprium, Teucrium pestalozzae, Thuja occidentalis, Thuja standishii, Thujopsis dolabrata, Thymbra capitata, Thymbra spicata, Thymus eigii, Thymus longicaulis, Thymus revolutus, Thymus sibthorpii, Thymus vulgaris, Thymus zygioides, Trachyspermum ammi, Trachyspermum anethifolium, Trichostema dichotomum, Tsuga heterophylla, Umbellularia californica, Valeriana officinalis, Vitex agnus-castus, Vitex negundo, Xenophyllum poposum, Xylopia aromatica, Zanthoxylum bungeanum, Zanthoxylum simulans, Zieria aspalathoides, Zingiber mioga and Zingiber officinale. It was first documented in 2006 (PMID: 16780354). Alpha-phellandrene, where both of them are endoocyclic) (PMID: 22978237) (PMID: 23074920) (PMID: 23162914) (PMID: 23285820).
Structure
Thumb
Synonyms
ValueSource
2-p-MenthadieneChEBI
3-Isopropyl-6-methylene-1-cyclohexeneChEBI
3-Methylene-6-(1-methylethyl)cyclohexeneChEBI
4-Isopropyl-1-methylene-2-cyclohexeneChEBI
beta-PhellandrenChEBI
b-PhellandrenGenerator
Β-phellandrenGenerator
b-PhellandreneGenerator
Β-phellandreneGenerator
3-Isopropyl-6-methylenecyclohexeneHMDB
3-Methylene-6-(1-methylethyl)-cyclohexeneHMDB
3-Methylidene-6-(propan-2-yl)cyclohex-1-eneHMDB
beta -PhellandreneHMDB
beta-Phellandrene, (-)-isomerHMDB
beta-Phellandrene, (+-)-isomerHMDB
Chemical FormulaC10H16
Average Mass136.2380 Da
Monoisotopic Mass136.12520 Da
IUPAC Name3-methylidene-6-(propan-2-yl)cyclohex-1-ene
Traditional Nameβ phellandrene
CAS Registry NumberNot Available
SMILES
CC(C)C1CCC(=C)C=C1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3
InChI KeyLFJQCDVYDGGFCH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies albaLOTUS Database
Abies balsameaLOTUS Database
Abies magnificaLOTUS Database
Abies nordmannianaLOTUS Database
Abies sachalinensisLOTUS Database
Abies sibiricaLOTUS Database
Achillea nobilisLOTUS Database
Agathosma betulinaLOTUS Database
Ageratum conyzoidesLOTUS Database
Aloysia citrodoraLOTUS Database
Anethum graveolensLOTUS Database
Angelica archangelicaLOTUS Database
Angelica dahuricaLOTUS Database
Artemisia santonicumLOTUS Database
Aspergillus candidusLOTUS Database
Aster scaberLOTUS Database
Atalantia buxifoliaLOTUS Database
Athamanta macedonicaLOTUS Database
Aucoumea klaineanaLOTUS Database
Austrobaileya scandensLOTUS Database
Bellis perennisLOTUS Database
Boronia latipinnaLOTUS Database
Bothriochloa bladhiiLOTUS Database
Brassica nigraLOTUS Database
Bunium persicumLOTUS Database
Bupleurum fruticosumLOTUS Database
Callistemon linearisLOTUS Database
Cannabis sativaLOTUS Database
Cantinoa mutabilisLOTUS Database
Catha edulisLOTUS Database
Chamaecyparis obtusaLOTUS Database
Chamaecyparis pisiferaLOTUS Database
Citrus aurantiumLOTUS Database
Citrus junosLOTUS Database
Citrus limonLOTUS Database
Citrus medicaLOTUS Database
Citrus natsudaidaiLOTUS Database
Citrus sinensisLOTUS Database
Cleistopholis patensLOTUS Database
Clinopodium carolinianumLOTUS Database
Coriandrum sativumLOTUS Database
Cotinus coggygriaLOTUS Database
Crithmum maritimumLOTUS Database
Cryptomeria japonicaLOTUS Database
Cuminum cyminumLOTUS Database
Cymbopogon flexuosusLOTUS Database
Dacrydium nausorienseLOTUS Database
Echinophora tenuifoliaLOTUS Database
Entandrophragma cylindricumLOTUS Database
Espeletia timotensisLOTUS Database
Etlingera elatiorLOTUS Database
Eucalyptus apodophyllaLOTUS Database
Eucalyptus camaldulensisLOTUS Database
Eucalyptus cloezianaLOTUS Database
Eucalyptus cneorifoliaLOTUS Database
Eucalyptus cunninghamiiLOTUS Database
Eucalyptus delegatensisLOTUS Database
Eucalyptus dolichorhynchaLOTUS Database
Eucalyptus porosaLOTUS Database
Eucalyptus punctataLOTUS Database
Eugenia dysentericaLOTUS Database
Ferula assa-foetidaLOTUS Database
Ferulago nodosaLOTUS Database
Ferulago trachycarpaLOTUS Database
Foeniculum vulgareLOTUS Database
Gossypium hirsutumLOTUS Database
Gossypium sturtianumLOTUS Database
Helichrysum taenariLOTUS Database
Heracleum dissectumLOTUS Database
Heracleum persicumLOTUS Database
Heterotheca subaxillarisLOTUS Database
Hyssopus officinalis L.LOTUS Database
Juniperus communisLOTUS Database
Juniperus drupaceaLOTUS Database
Juniperus excelsaLOTUS Database
Juniperus jaliscanaLOTUS Database
Juniperus monticolaLOTUS Database
Lantana camaraLOTUS Database
Larix gmeliniLOTUS Database
Larix gmelinii var. olgensisLOTUS Database
Larix kaempferiLOTUS Database
Larix occidentalisLOTUS Database
Larix sibiricaLOTUS Database
Laser trilobumLOTUS Database
Laurus nobilisLOTUS Database
Lavandula stoechasLOTUS Database
Lepechinia chamaedryoidesLOTUS Database
Lepechinia urbaniiLOTUS Database
Levisticum officinaleLOTUS Database
Ligusticum porteriLOTUS Database
Ligusticum sinenseLOTUS Database
Lindera neesianaLOTUS Database
Lippia rehmanniiLOTUS Database
Liquidambar styracifluaLOTUS Database
Liriodendron tulipiferaLOTUS Database
Machilus japonicaLOTUS Database
Magnolia balansaeLOTUS Database
Mangifera indicaLOTUS Database
Melaleuca alternifoliaLOTUS Database
Mentha aquaticaLOTUS Database
Mentha piperitaLOTUS Database
Mentha rotundifoliaLOTUS Database
Micromeria maderensisLOTUS Database
Micromeria teneriffaeLOTUS Database
Molopospermum peloponnesiacumLOTUS Database
Myrtus communisLOTUS Database
Nasutitermes ephrataeLOTUS Database
Ocimum americanumLOTUS Database
Oenanthe aquaticaLOTUS Database
Origanum acutidensLOTUS Database
Origanum hypericifoliumLOTUS Database
Origanum laevigatumLOTUS Database
Origanum onitesLOTUS Database
Origanum syriacumLOTUS Database
Origanum vulgareLOTUS Database
Parthenium confertumLOTUS Database
Pelargonium endlicherianumLOTUS Database
Pelargonium graveolensLOTUS Database
Pelargonium quercifoliumLOTUS Database
Pelargonium vitifoliumLOTUS Database
Petroselinum crispumLOTUS Database
Picea abiesLOTUS Database
Picea glehniiLOTUS Database
Picea koraiensisLOTUS Database
Picea schrenkianaLOTUS Database
Picea sitchensisLOTUS Database
Pimenta racemosaLOTUS Database
Pinus brutiaLOTUS Database
Pinus densifloraLOTUS Database
Pinus discolorLOTUS Database
Pinus elliottiiLOTUS Database
Pinus flexilisLOTUS Database
Pinus merkusiiLOTUS Database
Pinus monticolaLOTUS Database
Pinus pumilaLOTUS Database
Pinus rzedowskiiLOTUS Database
Pinus sylvestrisLOTUS Database
Piper auritumLOTUS Database
Piper fimbriulatumLOTUS Database
Piper guineenseLOTUS Database
Piper regnelliiLOTUS Database
Pistacia integerrimaLOTUS Database
Pistacia veraLOTUS Database
Pittosporum balfouriiLOTUS Database
Plagiochila rutilansLOTUS Database
Prangos uechtritziiLOTUS Database
Quercus ilexLOTUS Database
Renealmia alpiniaLOTUS Database
Rhanterium epapposumLOTUS Database
Rhodiola roseaLOTUS Database
Salvia africana-luteaLOTUS Database
Salvia columbariaeLOTUS Database
Salvia syriacaLOTUS Database
Santiria trimeraLOTUS Database
Santolina chamaecyparissusLOTUS Database
Santolina rosmarinifoliaLOTUS Database
Satureja cuneifoliaLOTUS Database
Satureja hortensis L.LOTUS Database
Satureja spicigeraLOTUS Database
Scalesia asperaLOTUS Database
Schinus molleLOTUS Database
Sequoia sempervirensLOTUS Database
Sequoiadendron giganteumLOTUS Database
Sideritis leucanthaLOTUS Database
Sideritis tragoriganumLOTUS Database
Skimmia laureolaLOTUS Database
Solidago odoraLOTUS Database
Stachys glutinosaLOTUS Database
Steganotaenia araliaceaLOTUS Database
Stoebe vulgarisLOTUS Database
Syzygium aromaticumLOTUS Database
Tagetes minutaLOTUS Database
Tanacetum millefoliumLOTUS Database
Tanacetum partheniumLOTUS Database
Tanacetum vulgareLOTUS Database
Targionia hypophyllaLOTUS Database
Teucrium cypriumLOTUS Database
Teucrium pestalozzaeLOTUS Database
Thuja occidentalisLOTUS Database
Thuja standishiiLOTUS Database
Thujopsis dolabrataLOTUS Database
Thymbra capitataLOTUS Database
Thymbra spicataLOTUS Database
Thymus eigiiLOTUS Database
Thymus longicaulisLOTUS Database
Thymus revolutusLOTUS Database
Thymus sibthorpiiLOTUS Database
Thymus vulgarisLOTUS Database
Thymus zygioidesLOTUS Database
Trachyspermum ammiLOTUS Database
Trachyspermum anethifoliumLOTUS Database
Trichostema dichotomumLOTUS Database
Tsuga heterophyllaLOTUS Database
Umbellularia californicaLOTUS Database
Valeriana officinalisLOTUS Database
Vitex agnus-castusLOTUS Database
Vitex negundoLOTUS Database
Xenophyllum poposumLOTUS Database
Xylopia aromaticaLOTUS Database
Zanthoxylum bungeanumLOTUS Database
Zanthoxylum simulansLOTUS Database
Zieria aspalathoidesLOTUS Database
Zingiber miogaLOTUS Database
Zingiber officinaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
logP3.98ALOGPS
logP3.26ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.75 m³·mol⁻¹ChemAxon
Polarizability17.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036081
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014917
KNApSAcK IDC00010872
Chemspider ID10669
KEGG Compound IDC19818
BioCyc IDBeta-phellandrene
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11142
PDB IDNot Available
ChEBI ID48741
Good Scents IDNot Available
References
General References
  1. Bergstrom MA, Luthman K, Nilsson JL, Karlberg AT: Conjugated dienes as prohaptens in contact allergy: in vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation. Chem Res Toxicol. 2006 Jun;19(6):760-9. doi: 10.1021/tx060006n. [PubMed:16780354 ]
  2. Marcetic M, Bozic D, Milenkovic M, Lakusic B, Kovacevic N: Chemical composition and antimicrobial activity of essential oil of different parts of Seseli rigidum. Nat Prod Commun. 2012 Aug;7(8):1091-4. [PubMed:22978237 ]
  3. Iscan G, Demirci B, Demirci F, Goger F, Kirimer N, Kose YB, Can Baser KH: Antimicrobial and antioxidant activities of Stachys lavandulifolia subsp. lavandulifolia essential oil and its infusion. Nat Prod Commun. 2012 Sep;7(9):1241-4. [PubMed:23074920 ]
  4. Tran HT, Nguyen SK, Nguyen TH, Tran MH, Nguyen TD: Chemical compositions of essential oils from Xyloselinum vietnamense and X. selinum leonidii. Nat Prod Commun. 2012 Oct;7(10):1373-4. [PubMed:23162914 ]
  5. Chizzola R: Composition of the essential oils from Peucedanum cervaria and P. alsaticum growing wild in the urban area of Vienna (Austria). Nat Prod Commun. 2012 Nov;7(11):1515-8. [PubMed:23285820 ]
  6. LOTUS database [Link]