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(-)-α-Terpineol

Cat No.:V40030 Purity: ≥98%
(-)-α-Terpineol ((S)-α-Terpineol) is a monoterpene compound, one of the compounds in Melaleuca alternifolia.
(-)-α-Terpineol
(-)-α-Terpineol Chemical Structure CAS No.: 10482-56-1
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of (-)-α-Terpineol:

  • α-Terpineol
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Top Publications Citing lnvivochem Products
Product Description
(-)-α-Terpineol ((S)-α-Terpineol) is a monoterpene compound, one of the compounds in Melaleuca alternifolia.
(-)-α-Terpineol is a naturally occurring monoterpenoid alcohol found in several medicinal plants such as Myrtus communis. It is one of the components responsible for the antifungal activity of tea tree (Melaleuca alternifolia) essential oil. With a molecular weight of 154.25 g/mol, this compound exhibits a variety of biological activities, including antitumor, anti-inflammatory, antimicrobial, and neuroprotective effects.
Biological Activity I Assay Protocols (From Reference)
Targets
(-)-α-Terpineol has been shown to have anticholinergic action and can block the interaction between PGE2 and GM1 receptors and cholera toxin. It inhibits the growth of tumor cells through a mechanism that involves inhibition of the NF-κB pathway. It also exhibits neuroprotective effects.
ln Vitro
(-)-α-Terpineol inhibits the growth of tumor cells through inhibition of the NF-κB pathway. It has demonstrated antimicrobial activity, particularly antifungal activity against pathogens. It also exhibits anti-inflammatory properties and neuroprotective effects.
ln Vivo
(-)-α-Terpineol exhibits cicatrizant activity in mice, showing wound healing properties with an effective dose (ED50) of 240.0 mg/kg as measured by tensile strength. It has antitumor, anti-inflammatory, and antimicrobial activities. Its neuroprotective effects suggest potential for neurological research.
Enzyme Assay
In vitro assays for (-)-α-Terpineol typically involve measuring its inhibition of tumor cell growth. Cancer cell lines are treated with increasing concentrations of the compound, and cell viability is assessed by MTT or CellTiter-Glo assays. Its antimicrobial activity is evaluated using broth microdilution or agar diffusion assays against various bacterial and fungal strains. NF-κB pathway inhibition can be assessed by reporter gene assays.
Cell Assay
For in vitro cell-based assays, cancer cell lines are cultured and treated with (-)-α-Terpineol at various concentrations. Cell viability is assessed by MTT assays. Apoptosis is evaluated by Annexin V/PI staining. Its anti-inflammatory effects are assessed by measuring cytokine production in LPS-stimulated immune cells. Its neuroprotective effects can be evaluated in neuronal cell cultures subjected to oxidative stress.
Animal Protocol
In vivo animal studies with (-)-α-Terpineol are conducted in models of cancer, inflammation, and wound healing. The compound is administered orally or intraperitoneally to rodents. Tumor growth inhibition, wound closure, and inflammatory markers are measured. Its cicatrizant activity has been demonstrated in mice.
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Following intravenous injection of a lethal dose of pine oil (0.1 mL/kg) into horses, the concentrations of α-terpineol in blood and tissues were observed to be 150–300 ppm. Following injection of a smaller dose of pine oil (0.033 mL/kg), the concentration in the blood decreased to undetectable levels after 2 hours, and no concentration was detected in tissues (time not specified).
(-)-α-Terpineol (CAS: 10482-56-1) has a molecular weight of 154.25 g/mol and a molecular formula of C10H18O. Appearance: colorless liquid. Purity: ≥98%. Storage: 2 years at -20°C as a liquid. The compound is a naturally occurring monoterpenoid with diverse biological activities.
Toxicity/Toxicokinetics
(-)-α-Terpineol is considered to have low toxicity and is generally recognized as safe (GRAS) as a flavoring agent. In preclinical studies, it has shown a favorable safety profile. No significant organ toxicity has been reported. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. 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.

[2]. The effect of α-terpineol enantiomers on biomarkers of rats fed a high-fat diet. Heliyon. 2020 Apr 30;6(4):e03752.

Additional Infomation
(S)-(-)-α-terpineol is the (S)-enantiomer of α-terpineol and is a plant metabolite. It is the enantiomer of (R)-(+)-α-terpineol. (-)-α-terpineol has been reported in Guarea macrophylla, Pinus densiflora, and other organisms with relevant data. See also: α-terpineol (note moved to).
(-)-α-Terpineol is a naturally occurring monoterpenoid alcohol with antitumor, anti-inflammatory, antimicrobial, and neuroprotective activities. It inhibits tumor cell growth through NF-κB pathway inhibition. It is not FDA-approved as a drug and is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H18O
Molecular Weight
154.2493
Exact Mass
154.135
CAS #
10482-56-1
Related CAS #
α-Terpineol;98-55-5
PubChem CID
443162
Appearance
Colorless to light yellow solid-liquid Mixture
Density
0.9±0.1 g/cm3
Boiling Point
217.5±0.0 °C at 760 mmHg
Melting Point
31-35ºC
Flash Point
89.4±0.0 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.483
LogP
2.79
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
1
Heavy Atom Count
11
Complexity
168
Defined Atom Stereocenter Count
1
SMILES
O([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C1([H])[H]
InChi Key
WUOACPNHFRMFPN-SECBINFHSA-N
InChi Code
InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m1/s1
Chemical Name
2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-ol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~648.30 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (16.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.4830 mL 32.4149 mL 64.8298 mL
5 mM 1.2966 mL 6.4830 mL 12.9660 mL
10 mM 0.6483 mL 3.2415 mL 6.4830 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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