Limonene

  • GreenMolBD CID : 43
  • Molecular Formula : C10H16
  • Molecular Weight : 136.238
  • Exact Molecular Mass : 136.125
  • IUPAC Name : 1-methyl-4-prop-1-en-2-ylcyclohexene
  • InChI : InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3
  • InChI Key : XMGQYMWWDOXHJM-UHFFFAOYSA-N
  • Canonical SMILES : CC1=CCC(CC1)C(=C)C
  • Isomeric SMILES : CC1=CCC(CC1)C(=C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound 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.

1.2. Taxonomy Tree

1.3. Alternative Parent

Monocyclic monoterpenoids; Branched unsaturated hydrocarbons; Cycloalkenes; Unsaturated aliphatic hydrocarbons;

1.4. Molecular Framework

Aliphatic homomonocyclic compounds

1.5. Substituents

P-menthane monoterpenoid; Monocyclic monoterpenoid; Branched unsaturated hydrocarbon; Cycloalkene; Cyclic olefin; Unsaturated aliphatic hydrocarbon; Unsaturated hydrocarbon; Olefin; Hydrocarbon; Aliphatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
3.3089 0 0 0 10 1 0 0 4.5912 232.488 170.819 0.585999

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-22.011369 0.31 -4.18 -9.40798 1.04769 5.228

4. Compound Reactivity

DLP nRFG nLMR
7 0 5

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Non-Toxic 2.58748 23211.2 0.066316 Moderate Weak None Degradable 0.00031533 2.1615

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes No Yes Yes Yes Yes

7. Synonyms

Name
Dipentene
Cinene
LIMONENE
138-86-3
Cajeputene
DL-Limonene
Kautschin
p-Mentha-1,8-diene
Dipenten
Polylimonene
Eulimen
Nesol
1,8-p-Menthadiene
Polydipentene
Cajeputen
Limonen
Cinen
Inactive limonene
Acintene DP dipentene
Dipanol
Unitene
alpha-Limonene
Flavor orange
Orange flavor
1,8(9)-p-Menthadiene
Limonene polymer
Cyclohexene, 1-methyl-4-(1-methylethenyl)-
Goldflush II
Acintene DP
Dipentene polymer
Di-p-mentha-1,8-diene
4-Isopropenyl-1-methyl-1-cyclohexene
(+/-)-Limonene
1-Methyl-4-(1-methylethenyl)cyclohexene
d,l-Limonene
1-Methyl-4-isopropenyl-1-cyclohexene
Dipentene 200
4-Isopropenyl-1-methylcyclohexene
Polymerized dipentene
(+-)-Dipentene
(+-)-Linonene
p-Mentha-1,8-diene, dl-
Caswell No. 526
Zonarez 7085
Zonarez 7115
delta-1,8-Terpodiene
(+-)-alpha-Limonene
MENTHA-1,8-DIENE (DL)
Dipentene, crude
.alpha.-Limonene
Limonene, dl-
DL-4-Isopropenyl-1-methylcyclohexene
NSC 21446
PC 560
1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, homopolymer
p-Mentha-1,8-diene, polymers
HSDB 1809
HSDB 1931
NSC 844
p-Mentha-1,8-diene, (+-)-
EINECS 205-341-0
EINECS 231-732-0
UN2052
.delta.-1,8-Terpodiene
1-Methyl-p-isopropenyl-1-cyclohexene
EPA Pesticide Chemical Code 079701
1-methyl-4-prop-1-en-2-ylcyclohexene
AI3-00739
7705-14-8
CHEBI:15384
XMGQYMWWDOXHJM-UHFFFAOYSA-N
4-isopropenyl-1-methyl-cyclohexene
C10H16
Limonene, (+)-
NCGC00163742-03
(1)-1-Methyl-4-(1-methylvinyl)cyclohexene
ST51046654
DSSTox_CID_9612
DSSTox_RID_78787
DSSTox_GSID_29612
8050-32-6
9003-73-0
beta-Limonene
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (.+/-.)-
Limonene, L-
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
d-Limonene (JAN)
555-08-8
8022-90-0
CAS-138-86-3
Terpenes and Terpenoids, limonene fraction
LEMON OIL
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-
DIPENTENE (+-)
Terpodiene
Ciene
a-limonene
Cyclil decene
Lemon extract
Lemon tincture
EINECS 227-815-6
Neroli oil
Orange oil
Cedro oil
Orange leaf oil
Citrus limon oil
Extract of lemon
Oil of lemon
Oil sweet orange
Oils, orange
Sweet orange oil
Oils, lemon
Achilles dipentene
Orange flower oil
Dipentene, tech.
Absolute petitgrain
Orange oil, sweet
Lemon oil, Guinea
65996-98-7
Citrus sinensis oil
Dipentene, technical, for use as solvent (for the paint industry), mixture of various terpenes
Lemon petigrain oil
Lemon oil, Italian
(?)-Limonene
Citrus limon extract
Lemon petitgrain oil
Neroli oil, pommade
Oil of sweet orange
AI3-25390
Mentha-1,8-diene
Absolue orange flower
Lemon oil concentrate
Lemon oil, distilled
Oils, citrus limonia
Oils, orange, sweet
Orange oil, distilled
p-Mentha-1, dl-
Dipentene, homopolymer
Orange flower absolute
Orange oil concentrate
Absolute orange flowers
(.+-.)-Limonene
Caswell No. 425A
d-Limonene (Limonene)
limonene, (S)-isomer
OIL OF ORANGE
Zitronen oel [German]
(.+-.)-Dipentene
1-Methyl-4-(1-methylethenyl)cyclohexene, (S)-
4-mentha-1,8-diene
Orange peel oil, sweet
Citrus sinensis peel oil
Petitgrain citronnier oil
AC1Q2ODZ
(.+/-.)-Dipentene
(.+/-.)-Limonene
DIPENTENE 38 PF
limonene, (+-)-isomer
Limonene, (+/-)-
Neat oil of sweet orange
ESSENCE DE PIN PF
DL-p-mentha-1,8-diene
Mentha-1,8-diene, DL
(+-)-(RS)-limonene
AC1L2K5B
AC1Q1J4Q
AC1Q1J4R
Cyclohexene, (.+-.)-
Dipentene, p.a., 95%
Orange sweet oil, expressed
Orange flower water absolute
p-Mentha-1,8(9)-diene
Orange oil, distilled, sweet
Orange oil, sweet, expressed
CCRIS 683
Dipentene, mixture of isomers
Sweet orange oil, terpeneless
CHEMBL15799
Monocyclic terpene hydrocarbons
Absolue orange flower decoloree
Citrus medica var. limonum oil
FEMA No. 2822
FEMA No. 2853
Methyl-4-isopropenylcyclohexene
NSC844
(.+/-.)-.alpha.-Limonene
Absolue orange flower from water
DTXSID2029612
Racemic: DL-limonene
(+/-)-p-Mentha-1,8-diene
CTK5C8417
HSDB 1934
HSDB 1944
KS-00000WVS
p-Mentha-1, (.+-.)-
NSC-844
1-Methyl-4-isopropenylcyclohexene
MolPort-001-782-985
HMS3264E05
Pharmakon1600-00307080
Methyl-4-isopropenyl-1-cyclohexene
NSC21446
Tox21_112068
Tox21_201818
Tox21_303409
c0626
MFCD00062992
NSC-21446
NSC757069
STK801934
1-methyl-4-isopropenylcyclohex-1-ene
AKOS009031280
Cyclohexene, 4-Isopropenyl-1-methyl-
Methyl-4-(1-methylethenyl)cyclohexene
WLN: L6UTJ A1 DY1 & U1
CCG-214016
EPA Pesticide Chemical Code 040501
EPA Pesticide Chemical Code 040517
LS-2278
LS-2880
MCULE-2462317444
NSC-757069
p-Mentha-1,8-diene, (.+/-.)-
p-Mentha-1,8-diene, polymers (8CI)
RP20299
UN 2052
d(R)-4-Isopropenyl-1-methylcyclohexene
Petitgrain bigarade sur fleurs d'oranger
(+/-)-p-Mentha-1,8-diene homopolymer
NCGC00163742-01
NCGC00163742-02
NCGC00163742-04
NCGC00257291-01
NCGC00259367-01
1-methyl-4-(1-methylethenyl)-cyclohexen
AK176153
AN-19448
AN-21149
AN-21151
AN-21831
AN-23147
BT000140
Dipentene [UN2052] [Flammable liquid]
LS-89490
LS-89491
LS-98217
NCI60_041856
OR012480
OR111377
OR111378
OR217376
OR339605
OR369142
p-Mentha-1,8-diene, homopolymer (7CI)
SC-80005
1-methyl-4-(1-methylethenyl) cylcohexene
1-methyl-4-(prop-1-en-2-yl)cyclohexene
4-(1-methylethenyl)-1-methyl-cyclohexene
Dipentene [UN2052] [Flammable liquid]
1-methyl-4-(1-methylvinyl)cyclohex-1-ene
Cyclohexene, 1-methyl-4-(1-methylethynyl)
Cyclohexene,1-methyl-4-(1-methylethenyl)-
lemon, oil (citrus limon (l.) burm. f.)
LS-180589
LS-181342
FT-0600409
L0046
EN300-21627
C06078
D00194
(s)-(-)-4-isopropenyl-1-methyl-1-cyclohexene
1-METHYL-4-PROP-1-EN-2-YL-CYCLOHEXENE
AB01563249_01
( inverted exclamation markA)-limonene(dipentene)
SR-01000872759
J-007186
J-520048
Petitgrain lemon oil (Citrus limon (L.) Burm. f.)
SR-01000872759-1
I14-18195
I14-53978
4B4F06FC-8293-455D-8FD5-C970CDB001EE
Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (+/-)-
Orange oil, terpeneless (Citrus sinensis (L.) Osbeck)
Cyclohexene,3-methyl-6-(1-methylethenyl)-, (3R,6R)-rel-
Limonene Solution, 1000 mg/L, 1 ml (RM, ISO GUIDE 34)
ORANGE PEEL, SWEET, OIL (CITRUS SINENSIS (L.) OSBECK)
ORANGE, OIL, DISTILLED (CITRUS SINENSIS (L.) OSBECK)
Dipentene, mixt. of limonene, 56-64%, and terpinolene, 20-25%
( inverted exclamation markA)-1,8-p-menthadiene,( inverted exclamation markA)-limonene
26123-39-7
68246-90-2
CS-0009072

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Limonene
Abelmoschus esculentus (L.) Moench Pod 3
Abelmoschus moschatus (L.) Medic. Seed 5
Ageratum conyzoides L Leaf; Aerial 1 , 2 , 17
Apium graveolens Aerial; Seed 8 , 2 , 3 , 4
Aquilaria malaccensis Wood 7
Coriandrum sativum Linn. Seed; Fruit; Aerial; Leaf 1 , 2 , 3 , 4 , 5 , 6 , 7 , 12 , 16 , 17 , 23 , 25 , 27 , 30 , 31 , 32 , 34 , 35
Curcuma amada Rhizome 1 , 4 , 5 , 7 , 9 , 15
Curcuma aromatica Salisb. Rhizome; Leaf; Petiole 1 , 8 , 9
Curcuma caesia Roxb. Leaf 2
Cuscuta reflexa Whole Plant 2
Cymbopogon citrates Leaf; Aerial; Blade; Sheath; Rhizome 1 , 2 , 11
Cyperus rotundus L Rhizome; Tuber 9 , 10 , 2 , 6 , 7
Helianthus annuus Flower 8
Hemidesmus indicus br. Root 5
Jatropha curcas L. Leaf; Aerial; Blade; Sheath; Rhizome 1 , 2 , 11
Juglans regia Leaf 13 , 14 , 17
Kaempferia parviflora Rhizome 5
Kalanchoe pinnata Leaf; Aerial; Blade; Sheath; Rhizome 1 , 2 , 11
Lantana camara L Leaf; Aerial; Seed 1 , 2 , 4
Leucas aspera Leaf; Aerial 2 , 3
Litchi chinensis Fruit 4 , 10
Luffa acutangula Flower 3
Magnolia grandiflora Flower 11
Mangifera indica Fruit Pulp; Fruit 6 , 7
Mentha arvensis Leaf; Shoot Stem; Shoot Leaaf; Stolon Stem; Stolon Leaf; Whole Plant; Stolon; Rhizome 1 , 2 , 3 , 6 , 8 , 9 , 11 , 14 , 15 , 16 , 17 , 18 , 19
Olea europea Leaf 4 , 6
Rosa damascena 14
Rumex vesicarius Aerial 1
Tamarindus indica Leaf 2
Viola odorata Leaf 5
Zanthoxylum rhetsa Seed 5

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
56 androgen receptor AR Homo sapiens 28.2808 743040
56 androgen receptor AR Homo sapiens 50.7207 743036
56 androgen receptor AR Homo sapiens 50.7207 743053
57 estrogen receptor 1 ESR1 Homo sapiens 9.0196 743075
57 estrogen receptor 1 ESR1 Homo sapiens 30.0771 743075
26 GLI family zinc finger 3 GLI3 Homo sapiens 71.0381 1259369
82 hypoxia inducible factor 1 subunit alpha HIF1A Homo sapiens 40.2889 1224846
28 lamin A/C LMNA Homo sapiens 0.7943 1487
29 nuclear factor kappa B subunit 1 NFKB1 Homo sapiens 63.8536 1159509
30 nuclear factor, erythroid 2 like 2 NFE2L2 Homo sapiens 630.957 720636
30 nuclear factor, erythroid 2 like 2 NFE2L2 Homo sapiens 1122.02 651741
83 nuclear receptor subfamily 1 group I member 2 NR1I2 Homo sapiens 562.341 720659
53 peroxisome proliferator activated receptor delta PPARD Homo sapiens 1258.93 588535
51 retinoic acid receptor alpha RARA Homo sapiens 13.3521 1159555
54 retinoid X receptor alpha RXRA Homo sapiens 5.0721 1159527
54 retinoid X receptor alpha RXRA Homo sapiens 16.0393 1159531
54 retinoid X receptor alpha RXRA Homo sapiens 1258.93 588544
47 thyroid hormone receptor beta THRB Homo sapiens 794.328 588547
81 tumor protein p53 TP53 Homo sapiens 3.1623 651743

10. Chemical Vendors

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316962870ParchemSource URLSource Detail13562Source Record URL
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332862065BiosynthSource URLSource DetailJ-007186Source Record URL
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85087295MP BiomedicalsSource URLSource Detail155234Source Record URL
56367668MP BiomedicalsSource URLSource Detail203318Source Record URL
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51073187MP BiomedicalsSource URLSource Detail209995Source Record URL
143801567TimTecSource URLSource DetailST51046654Source Record URL
254766185Boc SciencesSource URLSource Detail138-86-3Source Record URL
3587912401717 CheMall CorporationSource URLSource DetailBG03542739Source Record URL
3603386981717 CheMall CorporationSource URLSource DetailBG07179986Source Record URL
223684756AN PharmaTechSource URLSource DetailAN-19448Source Record URL
223675549AN PharmaTechSource URLSource DetailAN-21149Source Record URL
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346437972King ScientificSource URLSource DetailKS-00000WVSSource Record URL
347745837Yuhao ChemicalSource URLSource DetailJZ3299Source Record URL
347736249Yuhao ChemicalSource URLSource DetailJZ3330Source Record URL
347729122Yuhao ChemicalSource URLSource DetailLQ0986Source Record URL
347736032Yuhao ChemicalSource URLSource DetailLT5280Source Record URL
253217275MculeSource URLSource DetailMCULE-2462317444Source Record URL
24860056Sigma-AldrichSource URLSource Detail334111_ALDRICHSource Record URL
329756238Sigma-AldrichSource URLSource Detail42560_SIALSource Record URL
329828718Sigma-AldrichSource URLSource DetailV001621_VETECSource Record URL
24902101Sigma-AldrichSource URLSource DetailW524905_ALDRICHSource Record URL
321908579AcadechemSource URLSource DetailACDS-021543Source Record URL
174212588Angene ChemicalSource URLSource DetailAGN-PC-014NSBSource Record URL
355155060MuseChemSource URLSource DetailM069982Source Record URL
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3133093ChemExper Chemical DirectorySource URLSource DetailHeT@@DjWvifjih@@Source Record URL
318045679iChemical Technology USA IncSource URLSource DetailEBD46421Source Record URL
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126675987ChemMolSource URLSource Detail49414636Source Record URL
126677285ChemMolSource URLSource Detail49415934Source Record URL
342421172Wubei-BiochemSource URLSource DetailWB048856SUSource Record URL
125331072ISpharmSource URLSource DetailI14-18195Source Record URL
135378009ISpharmSource URLSource DetailI14-53978Source Record URL
145342543AKos Consulting & SolutionsSource URLSource DetailAKOS009031280Source Record URL
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104355628ABI ChemSource URLSource DetailAC1L2K5BSource Record URL
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318314540Chem-Space.com DatabaseSource URLSource DetailCSC000212220Source Record URL
354273066AbaChemSceneSource URLSource DetailCS-0009072Source Record URL
274953627ChemFacesSource URLSource DetailCFN93050Source Record URL
318169607labseekerSource URLSource DetailSC-80005Source Record URL
316542497abcr GmbHSource URLSource DetailAB354210Source Record URL
374180996AA BLOCKSSource URLSource DetailAA003OU0Source Record URL
57331137NovoSeekSource URLSource Detail22311Source Record URL
252326794AHH Chemical co.,ltdSource URLSource DetailMT-28656Source Record URL
164785589Finetech Industry LimitedSource URLSource DetailFT-0600409Source Record URL
318505062CambridgeChemSource URLSource DetailCB24450Source Record URL
290055262Aurora Fine Chemicals LLCSource URLSource DetailK05.594.369Source Record URL
348736632Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0254783Source Record URL
346551423LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00193967Source Record URL
162896734ChemTikSource URLSource DetailCTK5C8417Source Record URL
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