Terpineol

CAS# 98-55-5

Terpineol

Catalog No. BCN3595----Order now to get a substantial discount!

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Quality Control of Terpineol

Number of papers citing our products

Chemical structure

Terpineol

3D structure

Chemical Properties of Terpineol

Cas No. 98-55-5 SDF Download SDF
PubChem ID 442501 Appearance Colorless liquid
Formula C10H18O M.Wt 154.3
Type of Compound Monoterpenoids Storage Desiccate at -20°C
Synonyms p-Menth 1-ene 8-ol
Solubility DMSO : ≥ 250 mg/mL (1620.75 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol
SMILES CC1=CCC(CC1)C(C)(C)O
Standard InChIKey WUOACPNHFRMFPN-VIFPVBQESA-N
Standard InChI InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Terpineol

The branch of Eucalyptus globulus Labill.

Biological Activity of Terpineol

Descriptionα-Terpineol possesses antifungal activity against Trichophyton mentagrophytes, it also exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria. α-Terpineol shows anticonvulsant, and anti-inflammatory activities, it inhibits the gene expression of the IL-6 receptor.
TargetsIL Receptor | Antifection
In vitro

Effect of citral, eugenol, nerolidol and alpha-terpineol on the ultrastructural changes of Trichophyton mentagrophytes.[Pubmed: 19345255 ]

Fitoterapia. 2009 Jul;80(5):290-6.

The antifungal effects of citral, eugenol, nerolidol and alpha-Terpineol on Trichophyton mentagrophytes were investigated.
METHODS AND RESULTS:
Citral over 0.1 mg/ml strongly inhibited the hyphal growth of T. mentagrophytes, and the antifungal activity of alpha-Terpineol was less effective. The morphological changes of the fungus exposed to the terpenes were observed by electron microscopy. The hyphae were distorted and collapsed at 0.2, 0.4 and 1 mg/ml of eugenol, nerolidol and alpha-Terpineol respectively, and cell membrane and organelles were irreversibly damaged at 0.2 mg/ml citral.
CONCLUSIONS:
These suggested that four terpenes possess antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption.

Antimicrobial effect of linalool and α-terpineol against periodontopathic and cariogenic bacteria.[Pubmed: 22537719 ]

Anaerobe. 2012 Jun;18(3):369-72.


METHODS AND RESULTS:
Linalool and α-Terpineol exhibited strong antimicrobial activity against periodontopathic and cariogenic bacteria. However, their concentration should be kept below 0.4 mg/ml if they are to be used as components of toothpaste or gargling solution.
CONCLUSIONS:
Moreover, other compounds with antimicrobial activity against periodontopathic and cariogenic bacteria should be used in combination.

In vivo

Evolution of the Anticonvulsant Activity of α-Terpineol[Reference: WebLink]

Pharmaceutical Biology, 2007 , 45 (1) :69-70.

α-Terpineol, a monoterpenoid alcohol, was investigated for its anticonvulsant activity.
METHODS AND RESULTS:
This compound increased the latency to convulsions induced by pentylenetetrazole at doses of 100 and 200 mg/kg and decreased the incidence of hindlimb extension produced by MES in a dose-related manner at doses of 200 and 400 mg/kg.

Protocol of Terpineol

Kinase Assay

Characterization of alpha-terpineol as an anti-inflammatory component of orange juice by in vitro studies using oral buccal cells.[Pubmed: 17867636 ]

J Agric Food Chem. 2007 Oct 3;55(20):8040-6.


METHODS AND RESULTS:
Epithelial buccal cells (KB) were exposed to orange juice or orange juice fractions containing either the dry matter (DM), the volatile compounds (aqueous distillate, AD), or individual nonvolatile or volatile components. Intracellular formation of the pro-inflammatory cytokine IL-6 was analyzed by flow cytometry. Exposure to whole orange juice resulted in an increase in IL-6 formation of 23% compared to nontreated control cells, whereas treatment of the cells with either DM or AD resulted in a 22 or 1% increase, respectively. Dose-response experiments revealed that exposure of the cells to a 2- or 4-fold concentrated AD resulted in an increased IL-6 formation, whereas an inhibiting effect was measured after treatment of the cells with an 8-fold concentrated AD. These results indicated the presence of pro- as well as anti-inflammatory compounds in the aqueous distillate. To identify the active principles, volatile compounds present in the AD-treated cells were analyzed by GC-MS. In particular, limonene, linalool, and alpha-Terpineol were shown to be present in significant amounts. Subsequent studies on the IL-6 formation revealed that limonene had a stimulating effect and alpha-Terpineol had an inhibiting effect, whereas linalool had no effect.
CONCLUSIONS:
This anti-inflammatory effect of alpha-Terpineol on IL-6 formation was verified by quantitative real-time reverse transcription Polymerase Chain Reaction experiments in which alpha-Terpineol inhibited the gene expression of the IL-6 receptor.

Cell Research

Synergistic Effect and Mechanism of Cineole and Terpineol on In-vitro Transdermal Delivery of Huperzine A from Microemulsions.[Pubmed: 24250600]

Iran J Pharm Res. 2013 Spring;12(2):271-80.

The aim of the present study was to investigate the influence and the mechanisms of cineole and Terpineol on the in-vitro transdermal delivery of huperzine A from microemulsions, and their potential synergistic effect on the permeation enhancement.
METHODS AND RESULTS:
The transdermal delivery of huperzine A from microemulsions with different concentrations of cineole and Terpineol through the rat abdominal skin was determined by Franz-type diffusion cells. The partition coefficient of huperzine A between the full thickness skin and microemulsion was determined. Attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR) was carried out to analyze the effects of cineole and Terpineol on the biophysical properties of the stratum corneum (SC) and the mechanisms of permeation enhancement. These results indicated that cineole and Terpineol could synergistically increase the transdermal delivery of huperzine A from microemulsions through increasing the partition and diffusion coefficients of huperzine A. ATR-FTIR studies further validated the synergistic effect and revealed that the enhancing mechanisms were due to increasing the disorderliness and fluidity of SC lipid alkyl chains, disrupting the structure of keratin in SC, and extracting SC lipids.
CONCLUSIONS:
In conclusion, cineole and Terpineol, acting synergistically to enhance the transdermal delivery of huperzine A from microemulsions, might provide an alternative permeation enhancer combination for the transdermal delivery of huperzine A.

Terpineol Dilution Calculator

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Terpineol Molarity Calculator

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Preparing Stock Solutions of Terpineol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.4809 mL 32.4044 mL 64.8088 mL 129.6176 mL 162.022 mL
5 mM 1.2962 mL 6.4809 mL 12.9618 mL 25.9235 mL 32.4044 mL
10 mM 0.6481 mL 3.2404 mL 6.4809 mL 12.9618 mL 16.2022 mL
50 mM 0.1296 mL 0.6481 mL 1.2962 mL 2.5924 mL 3.2404 mL
100 mM 0.0648 mL 0.324 mL 0.6481 mL 1.2962 mL 1.6202 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Terpineol

Characterization of alpha-terpineol as an anti-inflammatory component of orange juice by in vitro studies using oral buccal cells.[Pubmed:17867636]

J Agric Food Chem. 2007 Oct 3;55(20):8040-6.

Epithelial buccal cells (KB) were exposed to orange juice or orange juice fractions containing either the dry matter (DM), the volatile compounds (aqueous distillate, AD), or individual nonvolatile or volatile components. Intracellular formation of the pro-inflammatory cytokine IL-6 was analyzed by flow cytometry. Exposure to whole orange juice resulted in an increase in IL-6 formation of 23% compared to nontreated control cells, whereas treatment of the cells with either DM or AD resulted in a 22 or 1% increase, respectively. Dose-response experiments revealed that exposure of the cells to a 2- or 4-fold concentrated AD resulted in an increased IL-6 formation, whereas an inhibiting effect was measured after treatment of the cells with an 8-fold concentrated AD. These results indicated the presence of pro- as well as anti-inflammatory compounds in the aqueous distillate. To identify the active principles, volatile compounds present in the AD-treated cells were analyzed by GC-MS. In particular, limonene, linalool, and alpha-Terpineol were shown to be present in significant amounts. Subsequent studies on the IL-6 formation revealed that limonene had a stimulating effect and alpha-Terpineol had an inhibiting effect, whereas linalool had no effect. This anti-inflammatory effect of alpha-Terpineol on IL-6 formation was verified by quantitative real-time reverse transcription Polymerase Chain Reaction experiments in which alpha-Terpineol inhibited the gene expression of the IL-6 receptor.

Synergistic Effect and Mechanism of Cineole and Terpineol on In-vitro Transdermal Delivery of Huperzine A from Microemulsions.[Pubmed:24250600]

Iran J Pharm Res. 2013 Spring;12(2):271-80.

The aim of the present study was to investigate the influence and the mechanisms of cineole and Terpineol on the in-vitro transdermal delivery of huperzine A from microemulsions, and their potential synergistic effect on the permeation enhancement. The transdermal delivery of huperzine A from microemulsions with different concentrations of cineole and Terpineol through the rat abdominal skin was determined by Franz-type diffusion cells. The partition coefficient of huperzine A between the full thickness skin and microemulsion was determined. Attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR) was carried out to analyze the effects of cineole and Terpineol on the biophysical properties of the stratum corneum (SC) and the mechanisms of permeation enhancement. These results indicated that cineole and Terpineol could synergistically increase the transdermal delivery of huperzine A from microemulsions through increasing the partition and diffusion coefficients of huperzine A. ATR-FTIR studies further validated the synergistic effect and revealed that the enhancing mechanisms were due to increasing the disorderliness and fluidity of SC lipid alkyl chains, disrupting the structure of keratin in SC, and extracting SC lipids. In conclusion, cineole and Terpineol, acting synergistically to enhance the transdermal delivery of huperzine A from microemulsions, might provide an alternative permeation enhancer combination for the transdermal delivery of huperzine A.

Antimicrobial effect of linalool and alpha-terpineol against periodontopathic and cariogenic bacteria.[Pubmed:22537719]

Anaerobe. 2012 Jun;18(3):369-72.

Linalool and alpha-Terpineol exhibited strong antimicrobial activity against periodontopathic and cariogenic bacteria. However, their concentration should be kept below 0.4 mg/ml if they are to be used as components of toothpaste or gargling solution. Moreover, other compounds with antimicrobial activity against periodontopathic and cariogenic bacteria should be used in combination.

Effect of citral, eugenol, nerolidol and alpha-terpineol on the ultrastructural changes of Trichophyton mentagrophytes.[Pubmed:19345255]

Fitoterapia. 2009 Jul;80(5):290-6.

The antifungal effects of citral, eugenol, nerolidol and alpha-Terpineol on Trichophyton mentagrophytes were investigated. Citral over 0.1 mg/ml strongly inhibited the hyphal growth of T. mentagrophytes, and the antifungal activity of alpha-Terpineol was less effective. The morphological changes of the fungus exposed to the terpenes were observed by electron microscopy. The hyphae were distorted and collapsed at 0.2, 0.4 and 1 mg/ml of eugenol, nerolidol and alpha-Terpineol respectively, and cell membrane and organelles were irreversibly damaged at 0.2 mg/ml citral. These suggested that four terpenes possess antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption.

Description

α-Terpineol is isolated from Eucalyptus globulus Labill, exhibits strong antimicrobial activity against periodontopathic and cariogenic bacteria. α-Terpineol possesses antifungal activity against T. mentagrophytes, and the activity might lead to irreversible cellular disruption.

Keywords:

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