alpha-Terpineol

  • GreenMolBD CID : 58
  • Molecular Formula : C10H18O
  • Molecular Weight : 154.253
  • Exact Molecular Mass : 154.136
  • IUPAC Name : 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol
  • InChI : InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
  • InChI Key : WUOACPNHFRMFPN-UHFFFAOYSA-N
  • Canonical SMILES : CC1=CCC(CC1)C(C)(C)O
  • Isomeric SMILES : CC1=CCC(CC1)C(C)(C)O
  • 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; Tertiary alcohols; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homomonocyclic compounds

1.5. Substituents

P-menthane monoterpenoid; Monocyclic monoterpenoid; Tertiary alcohol; Organic oxygen compound; Hydrocarbon derivative; Organooxygen compound; Alcohol; Aliphatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
2.5037 20.23 1 1 11 1 0 0 4.73958 246.912 187.414 0.624728

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-96.559569 1.43 -4.046 -9.3021 1.21076 5.256

4. Compound Reactivity

DLP nRFG nLMR
4 0 4

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)
Carcinogen Non-Mutagen Toxic 1.36699 12191.5 0.0188461 Moderate Weak None Degradable 0.0139016 11.8226

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
alpha-TERPINEOL
Terpineol
98-55-5
p-Menth-1-en-8-ol
2-(4-methylcyclohex-3-en-1-yl)propan-2-ol
dl-alpha-Terpineol
1-p-Menthen-8-ol
1-Menthene-8-ol
Terpineol schlechthin
CARVOMENTHENOL
Terpenol
TERPINEOLS
.alpha.-Terpineol
Terpilenol, alpha-
Terpineol 350
1-Methyl-4-isopropyl-1-cyclohexen-8-ol
2-(4-Methyl-3-cyclohexenyl)-2-propanol
alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol
Terpene alcohol
FEMA Number 3045
1-Methyl-4-isopropyl-1-cyclohexene-8-ol
alpha-Terpineol (natural)
8000-41-7
FEMA No. 3045
alpha-Terpinenol
CCRIS 3204
HSDB 5316
Mixture of p-methenols
1-alpha-terpineol
EINECS 202-680-6
EINECS 219-448-5
NSC 21449
PC 593
3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-
BRN 1906604
AI3-00275
CHEBI:22469
WUOACPNHFRMFPN-UHFFFAOYSA-N
Alpha-Terpineol, Mixture of Isomers
MFCD00001557
MFCD00166983
SBB061191
3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-
NCGC00164431-01
DSSTox_CID_6625
DSSTox_RID_79596
DSSTox_GSID_40775
(1)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanol
a-Terpineol
alpha-Terpineol, analytical standard
Menth-1-en-8-ol
22347-88-2
8006-39-1
CAS-8000-41-7
3-Cyclohexene-1-methanol,.alpha.4-trimethyl-
Caswell No. 823
Terpineol Normal
DL a-terpineol
2-(4-methylcyclohex-3-enyl)propan-2-ol
EINECS 232-268-1
Terpineol (natural)
EPA Pesticide Chemical Code 067005
1-.alpha.-Terpineol
TERPINEOL OR
TERPINEOL, ALPHA
d-1-p-Menthen-8-ol
Terpineol, mixed isomers
Monocyclic terpenealcohols
(+)-.alpha.-Terpineol
p-Menth- 1-en-8-ol
3-Cyclohexene-1-methanol, ?,?,4-trimethyl-
3-Cyclohexene-1-methanol, .alpha.,.alpha.4-trimethyl-
alpha-Terpineol, AldrichCPR
DSSTox_RID_78167
DSSTox_GSID_26625
SCHEMBL28466
KSC486Q4B
3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (1S)-
3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (S)-
AC1L29B5
CHEMBL449810
DTXSID5026625
CTK3I6840
KS-00000FMH
MolPort-002-042-108
NSC21449
Tox21_112118
Tox21_200112
Tox21_302298
NSC-21449
NSC403665
3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, sodium salt, (1S)-
4-Trimethyl-3-cyclohexene-1-methanol
68540-43-2 (hydrochloride salt)
AKOS015840815
alpha-Terpineol, 90%, technical grade
LS-3106
MCULE-9798755896
NSC-403665
CAS-98-55-5
NCGC00248528-01
NCGC00255464-01
NCGC00257666-01
11103-96-1
AK122298
AN-18294
AN-19422
AN-24486
OR034447
OR126371
OR342936
OR343294
SC-46794
KB-223071
LS-148797
TR-030336
FT-0622202
FT-0698995
ST24039469
ST50824481
V0385
2-(4-methyl-1-cyclohex-3-enyl)-propan-2-ol
C16772
(1R)-a,a,4-trimethyl-3-cyclohexene-1-methanol
SR-01000944873
J-500272
SR-01000944873-1
W-100076
3-Cyclohexene-1-methanol, ?,?,4-trimethyl-, (R)-
3-Cyclohexene-1-methanol, ?,?,4-trimethyl-, (S)-
I14-51686
F0001-2319
alpha-Terpineol, primary pharmaceutical reference standard
3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, (1R)-
3-Cyclohexene-1-methanol, .alpha.,.alpha.,4-trimethyl-, sodium salt (1:1), (1S)-
2438-12-2
37195-01-0
8031-32-1
68797-63-7
EC 202-680-6
EC 232-268-1
c0669

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
alpha-Terpineol
Abelmoschus esculentus (L.) Moench Pod 3
Abelmoschus moschatus (L.) Medic. Seed 5
Ageratum conyzoides L Leaf; Aerial 1 , 17
Anisomeles indica (L.) Kuntze. Flower 11
Annona reticulata L. Leaf 10
Apium graveolens Aerial; Seed 2 , 3 , 4
Corchorus olitorius L. Leaf 10
Coriandrum sativum Linn. Seed; Fruit; Root 1 , 2 , 4 , 6 , 7 , 10 , 12 , 13 , 19 , 25 , 27 , 29 , 32 , 33
Curculigo orchioides Leaf 10
Curcuma amada Rhizome 4 , 7 , 9 , 15
Curcuma aromatica Salisb. Leaf; Rhizome; Petiole 7 , 8
Curcuma caesia Roxb. Leaf 2
Curcuma longa L. Leaf 10
Cuscuta reflexa Whole Plant 2
Cymbopogon citrates Aerial; Blade; Sheath; Rhizome 2
Cyperus rotundus L Tuber 6 , 7
Ficus carica L. Leaf 10
Ficus religiosa Leaf 10
Garcinia mangostana Leaf 10
Helianthus annuus Flower 8
Hemidesmus indicus br. Root 6
Jasminum graniflorum Flower 20 , 22
Jasminum sambac L. Flower 5
Jatropha curcas L. Aerial; Blade; Sheath; Rhizome 2
Juglans regia Leaf 13
Kaempferia parviflora Rhizome 5
Kalanchoe pinnata Aerial; Blade; Sheath; Rhizome 2
Lactuca sativa L. Leaf 10
Lantana camara L Aerial; Leaf and Flower; Seed 2 , 3 , 4
Lepidium sativum Seed 5
Leucas aspera Aerial 3
Lippia nodiflora (L.) Pod 2
Litchi chinensis Fruit 4 , 11
Luffa acutangula Flower 3
Lycopersicon lycopersicum Leaf 10
Magnolia grandiflora Flower 11
Mangifera indica Fruit 7
Mentha arvensis Leaf; Shoot Stem; Shoot Leaf; Stolon Stem; Stolon Leaf; Stolon; Rhizome 1 , 2 , 3 , 9 , 11 , 12 , 17 , 18 , 19
Michelia champaca Leaf 10
Musa paradisiaca Leaf 10
Olea europea Leaf 2 , 6
Phoenix dactylifera Leaf 10
Phyllanthus embelica Leaf 10
Piper betel Leaf 10
Piper nigrum Leaf 10
Punica granatum Leaf 10
Rauvolfia serpentine Leaf 10
Rheum emodi Leaf 10
Rosa damascena Flower; Petal 4 , 6 , 7 , 11 , 12 , 14
Ruellia tuberosa Leaf 10
Semicarpus anacardium Leaf 1
Tamarindus indica Leaf; Fruit; pulp 2 , 9 , 10 , 12
Viola odorata Flower; Leaf 2 , 5
Zanthoxylum rhetsa Seed Coat; Seed 3 , 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
26 GLI family zinc finger 3 GLI3 Homo sapiens 0.615 1259369
26 GLI family zinc finger 3 GLI3 Homo sapiens 76.9588 1259369
28 lamin A/C LMNA Homo sapiens 0.0035 1487
55 nuclear receptor subfamily 3 group C member 1 NR3C1 Homo sapiens 13.4481 720691
50 RAR-related orphan receptor gamma Rorc Mus musculus 0.0031 1159521
81 tumor protein p53 TP53 Homo sapiens 76.9588 651631

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
346565787LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN00196317Source Record URL
310280651Glentham Life Sciences Ltd.Source URLSource DetailGL0054Source Record URL
310280653Glentham Life Sciences Ltd.Source URLSource DetailGL1816Source Record URL
329747630Sigma-AldrichSource URLSource Detail03420590_SIALSource Record URL
329747989Sigma-AldrichSource URLSource Detail04899_SIALSource Record URL
329753548Sigma-AldrichSource URLSource Detail30627_SIALSource Record URL
24867093Sigma-AldrichSource URLSource Detail432628_ALDRICHSource Record URL
329778478Sigma-AldrichSource URLSource DetailCDS001264_ALDRICHSource Record URL
347758676Alfa ChemistrySource URLSource Detail98-55-5Source Record URL
253217592MculeSource URLSource DetailMCULE-9798755896Source Record URL
312606147Oakwood ProductsSource URLSource Detail320108Source Record URL
89085057MolPortSource URLSource DetailMolPort-002-042-108Source Record URL
172872485Nanjing KaimuboSource URLSource DetailKB-223071Source Record URL
3632033111717 CheMall CorporationSource URLSource DetailBG04165550Source Record URL
3627698331717 CheMall CorporationSource URLSource DetailBG04455359Source Record URL
3603801071717 CheMall CorporationSource URLSource DetailBG07221395Source Record URL
162755158ChemTikSource URLSource DetailCTK3I6840Source Record URL
316439196abcr GmbHSource URLSource DetailAB203948Source Record URL
316579099abcr GmbHSource URLSource DetailAB393319Source Record URL
85089727MP BiomedicalsSource URLSource Detail156753Source Record URL
56371269MP BiomedicalsSource URLSource Detail218932Source Record URL
253657446Bestdo IncSource URLSource Detailalpha terpineolSource Record URL
354289382Chemenu Inc.Source URLSource DetailCM115916Source Record URL
249858917SyntreeSource URLSource DetailST24039469Source Record URL
354325305iChemical Technology USA IncSource URLSource DetailEBD2294054Source Record URL
162091615Chembase.cnSource URLSource Detail104673Source Record URL
346428564King ScientificSource URLSource DetailKS-00000FMHSource Record URL
163807027King ScientificSource URLSource DetailKSC486Q4BSource Record URL
312338889BiosynthSource URLSource DetailJ-500272Source Record URL
255370900BiosynthSource URLSource DetailW-100076Source Record URL
316962903ParchemSource URLSource Detail13864Source Record URL
316963006ParchemSource URLSource Detail14183Source Record URL
316965078ParchemSource URLSource Detail25165Source Record URL
347811614Life ChemicalsSource URLSource DetailF0001-2319Source Record URL
223653636AN PharmaTechSource URLSource DetailAN-18294Source Record URL
223681460AN PharmaTechSource URLSource DetailAN-19422Source Record URL
223686461AN PharmaTechSource URLSource DetailAN-24486Source Record URL
318359359CambridgeChemSource URLSource DetailB113601Source Record URL
329972343CambridgeChemSource URLSource Detailwkq-01058Source Record URL
87576046TCI (Tokyo Chemical Industry)Source URLSource DetailT0022Source Record URL
87576795TCI (Tokyo Chemical Industry)Source URLSource DetailT0984Source Record URL
347745033Yuhao ChemicalSource URLSource DetailXJ4674Source Record URL
126672692ChemMolSource URLSource Detail49411341Source Record URL
126673725ChemMolSource URLSource Detail49412374Source Record URL
126678630ChemMolSource URLSource Detail49417279Source Record URL
241151770ChemMolSource URLSource Detail99160874Source Record URL
241176306ChemMolSource URLSource Detail99185410Source Record URL
29204607R&D ChemicalsSource URLSource Detail5066Source Record URL
151980234AKos Consulting & SolutionsSource URLSource DetailAKOS015840815Source Record URL
349517919Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM1036061Source Record URL
318257351Chem-Space.com DatabaseSource URLSource DetailCSC000036307Source Record URL
342421174Wubei-BiochemSource URLSource DetailWU020179CASource Record URL
252073455Bide Pharmatech Ltd.Source URLSource DetailBD113601Source Record URL
164806311Finetech Industry LimitedSource URLSource DetailFT-0622202Source Record URL
273223017Finetech Industry LimitedSource URLSource DetailFT-0698995Source Record URL
135563901TractusSource URLSource DetailTR-030336Source Record URL
255445740OXCHEM CORPORATIONSource URLSource DetailAX8113601Source Record URL
275927082BePharm Ltd.Source URLSource DetailB113601Source Record URL
162187718AK Scientific, Inc. (AKSCI)Source URLSource DetailV0385Source Record URL
250217256Founder PharmaSource URLSource DetailFD33182Source Record URL
135377144ISpharmSource URLSource DetailI14-51686Source Record URL
143435221TimTecSource URLSource DetailSBB061191Source Record URL
143857001TimTecSource URLSource DetailST50824481Source Record URL
318168082labseekerSource URLSource DetailSC-46794Source Record URL
349997679Fisher ChemicalSource URLSource DetailT311Source Record URL
347825011Achemo Scientific LimitedSource URLSource DetailAC-94434Source Record URL
289685283Aurora Fine Chemicals LLCSource URLSource DetailK02.100.342Source Record URL
369107959AmbinterSource URLSource DetailAmb2404780Source Record URL
3138535ChemExper Chemical DirectorySource URLSource DetailHmtH@@rJQPiXYjjih@@Source Record URL
57329640NovoSeekSource URLSource Detail17100Source Record URL
252256548Wilshire TechnologiesSource URLSource Detailalpha-TerpineolSource Record URL
254788100Boc SciencesSource URLSource Detail98-55-5Source Record URL
104341582ABI ChemSource URLSource DetailAC1L29B5Source Record URL
355435776MuseChemSource URLSource DetailR015858Source Record URL