NP-MRD: Showing NP-Card for (-)-4-terpineol (NP0218376)

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Record Information

Version

2.0

Created at

2022-09-05 19:01:53 UTC

Updated at

2022-09-05 19:01:53 UTC

NP-MRD ID

NP0218376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-4-terpineol

Description

(-)-Terpinen-4-ol, also known as terpinenol-4, 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. (-)-4-terpineol is found in Callitropsis nootkatensis, Citrus unshiu, Cryptomeria japonica, Leptospermum scoparium, Ligusticum chuanxiong, Lychnophora ericoides, Melaleuca alternifolia, Myrtus communis and Thymus marschallianus. (-)-4-terpineol was first documented in 2020 (PMID: 32956790). The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (-)-Terpinen-4-ol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32947397) (PMID: 32924099) (PMID: 32901989) (PMID: 32895862).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.7359   -0.1210   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.1021    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672   -1.2052    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548   -1.0373    0.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    0.0610   -0.2075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3419   -0.3640   -1.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224    0.1469    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7320    1.0944   -0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5749   -1.2177    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2770    1.3283    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6345    1.1512    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9392   -1.1224   -0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3721    0.0763    0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    0.6665   -0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -2.1394   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1000   -0.6867    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028   -1.9727    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786   -1.3503   -1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484    0.4761    1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    0.5698   -1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496    1.8939   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5139    1.5793    0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848   -1.0835    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2985   -1.7256   -0.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505   -1.8295    1.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911    2.0257    0.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4644    1.8053   -0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2859    2.0093    0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5274    1.0735    1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  7  5  1  0
  5  6  1  6
  5 10  1  0
 10 11  1  0
 11  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  7 19  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
  6 18  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
M  END

View in JSmol

Synonyms

Value	Source
Terpinen-4-ol	MeSH
(R)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol	MeSH
Terpinenol-4	MeSH
(1R)-4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol	PhytoBank
(-)-4-Terpineol	PhytoBank
(-)-Terpinen-4-ol	PhytoBank
(R)-(-)-p-Menth-1-en-4-ol	PhytoBank
(R)-4-Carvomenthenol	PhytoBank
(R)-4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol	PhytoBank
(R)-Terpinen-4-ol	PhytoBank
l-4-Terpineol	PhytoBank
l-4-Terpineneol	PhytoBank
l-Terpinen-4-ol	PhytoBank
p-Menth-1-en-4-ol	PhytoBank
4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol	PhytoBank
(±)-4-Terpineol	PhytoBank
(±)-Terpinen-4-ol	PhytoBank
1-(1-Methylethyl)-4-methyl-3-cyclohexen-1-ol	PhytoBank
1-Isopropyl-4-methylcyclohex-3-en-1-ol	PhytoBank
1-Terpen-4-ol	PhytoBank
1-Terpinen-4-ol	PhytoBank
4-Carvomenthenol	PhytoBank
4-Methyl-1-(1-methylethyl)-3-cyclohexene-1-ol	PhytoBank
4-Methyl-1-isopropyl-3-cyclohexen-1-ol	PhytoBank
4-Terpinenol	PhytoBank
4-Terpineol	PhytoBank
Melaleucol	PhytoBank
Terpin-4-ol	PhytoBank
Terpinene-4-ol	PhytoBank
Terpineol-4	PhytoBank
dl-4-Terpineol	PhytoBank

Chemical Formula

C₁₀H₁₈O

Average Mass

154.2530 Da

Monoisotopic Mass

154.13577 Da

IUPAC Name

(1R)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

Traditional Name

(1R)-1-isopropyl-4-methylcyclohex-3-en-1-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@]1(O)CCC(C)=CC1

InChI Identifier

InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m0/s1

InChI Key

WRYLYDPHFGVWKC-JTQLQIEISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Callitropsis nootkatensis	LOTUS Database	35616633
Citrus unshiu	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Leptospermum scoparium	LOTUS Database	35616633
Ligusticum chuanxiong	LOTUS Database	35616633
Lychnophora ericoides	LOTUS Database	35616633
Melaleuca alternifolia	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Thymus marschallianus	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

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	2.81	ALOGPS
logP	2.33	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	20	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.31 m³·mol⁻¹	ChemAxon
Polarizability	18.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4483313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5325830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ed-Dra A, Filali FR, Lo Presti V, Zekkori B, Nalbone L, Bouymajane A, Trabelsi N, Lamberta F, Bentayeb A, Giuffrida A, Giarratana F: Chemical composition, antioxidant capacity and antibacterial action of five Moroccan essential oils against Listeria monocytogenes and different serotypes of Salmonella enterica. Microb Pathog. 2020 Dec;149:104510. doi: 10.1016/j.micpath.2020.104510. Epub 2020 Sep 18. [PubMed:32956790 ]
Chen D, Wang J, Sullivan DA, Kam WR, Liu Y: Effects of Terpinen-4-ol on Meibomian Gland Epithelial Cells In Vitro. Cornea. 2020 Dec;39(12):1541-1546. doi: 10.1097/ICO.0000000000002506. [PubMed:32947397 ]
de Assis KMA, da Silva Leite JM, de Melo DF, Borges JC, Santana LMB, Dos Reis MML, Moreira VM, da Rocha WRV, Catao RMR, Dos Santos SG, da Silva Portela A, de Sousa Silva SM, de Oliveira TKB, de Souza da Silveira JW, Pires EG, Nonaka CFW, Sanches FAC, de Lima Damasceno BPG: Bicontinuous microemulsions containing Melaleuca alternifolia essential oil as a therapeutic agent for cutaneous wound healing. Drug Deliv Transl Res. 2020 Dec;10(6):1748-1763. doi: 10.1007/s13346-020-00850-0. Epub 2020 Sep 13. [PubMed:32924099 ]
Ribeiro VP, Arruda C, Mejia JAA, Candido ACBB, Dos Santos RA, Magalhaes LG, Bastos JK: Brazilian southeast brown propolis: gas chromatography method development for its volatile oil analysis, its antimicrobial and leishmanicidal activities evaluation. Phytochem Anal. 2021 May;32(3):404-411. doi: 10.1002/pca.2988. Epub 2020 Sep 9. [PubMed:32901989 ]
Huang J, Yang L, Zou Y, Luo S, Wang X, Liang Y, Du Y, Feng R, Wei Q: Antibacterial activity and mechanism of three isomeric terpineols of Cinnamomum longepaniculatum leaf oil. Folia Microbiol (Praha). 2021 Feb;66(1):59-67. doi: 10.1007/s12223-020-00818-0. Epub 2020 Sep 7. [PubMed:32895862 ]
LOTUS database [Link]

Showing NP-Card for (-)-4-terpineol (NP0218376)

MOL for NP0218376 ((-)-4-terpineol)

3D MOL for NP0218376 ((-)-4-terpineol)

3D SDF for NP0218376 ((-)-4-terpineol)

3D-SDF for NP0218376 ((-)-4-terpineol)

PDB for NP0218376 ((-)-4-terpineol)

3D PDB for NP0218376 ((-)-4-terpineol)

SMILES for NP0218376 ((-)-4-terpineol)

INCHI for NP0218376 ((-)-4-terpineol)

Structure for NP0218376 ((-)-4-terpineol)

3D Structure for NP0218376 ((-)-4-terpineol)