Patchouli alcohol

CAS# 5986-55-0

Patchouli alcohol

Catalog No. BCN4966----Order now to get a substantial discount!

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Quality Control of Patchouli alcohol

Number of papers citing our products

Chemical structure

Patchouli alcohol

3D structure

Chemical Properties of Patchouli alcohol

Cas No. 5986-55-0 SDF Download SDF
PubChem ID 442384 Appearance White-pale yellow powder
Formula C15H26O M.Wt 222.36
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Synonyms Patchoulol
Solubility Freely soluble in chloroform; soluble in ethanol and methanol; insoluble in water
SMILES CC1CCC2(C(C3CCC2(C1C3)C)(C)C)O
Standard InChIKey GGHMUJBZYLPWFD-DUNKBJDJSA-N
Standard InChI InChI=1S/C15H26O/c1-10-5-8-15(16)13(2,3)11-6-7-14(15,4)12(10)9-11/h10-12,16H,5-9H2,1-4H3/t10-,11?,12?,14-,15?/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 Patchouli alcohol

1 Valeriana sp.

Biological Activity of Patchouli alcohol

DescriptionPatchouli alcohol has anti-inflammatory, neuroprotective, anti-cancer, anti-oxidant, gastroprotective, immunomodulatory, and antibacterial effects, which may be mediated, at least in part, by down-regulation of the mRNA expression of a panel of inflammatory mediators, such as TNF-α, IL-1β, IL-6, iNOS and COX-2. Patchouli alcohol significantly accelerates the recovery of the UV-induced skin lesions, evidently through anti-oxidant and anti-inflammatory action, as well as down-regulation of the MMP-1 and MMP-3 expression.
TargetsTNF-α | PGE | COX | IL Receptor | SOD | MMP(e.g.TIMP) | CDK | p65 | NF-kB | HDAC | c-Myc | NO | NOS | Antifection
In vitro

Patchouli alcohol, an essential oil of Pogostemon cablin, exhibits anti-tumorigenic activity in human colorectal cancer cells.[Pubmed: 23602914]

Int Immunopharmacol. 2013 Jun;16(2):184-90.

Patchouli alcohol (PA) is one of the important compounds isolated from the essential oil of Pogostemon cablin (patchouli). PA has neuroprotective, anti-influenza and anti-inflammatory activities. However, anti-cancer activity of PA has not been studied so far. We performed in vitro study to investigate whether PA affects proliferation and apoptosis of human colorectal cancer cells, and to define potential molecular mechanisms.
METHODS AND RESULTS:
PA suppressed cell growth and induced apoptosis in a dose-dependent manner in human colorectal cancer cells (HCT116, SW480). In addition, PA decreased cell growth in MCF7, BxPC3, PC3, and HUVEC cells. Exposure of PA to HCT116 and SW480 cells activated p21 expression and suppressed the expressions of cyclin D1 and cyclin-dependent kinase 4 (CDK4) in a dose-dependent manner. In addition, PA attenuated the expressions of HDAC2 (histone deacetylase 2) and c-myc, and HDAC enzyme activity. We also observed that PA induced the transcriptional activity of NF-κB through an increase of nuclear translocation of p65.
CONCLUSIONS:
These findings suggest that PA exerts an anti-cancer activity by decreasing cell growth and increasing apoptosis in human colorectal cancer cells. The proposed mechanisms include the inhibition of HDAC2 expression and HDAC enzyme activity, and subsequent downregulation of c-myc and activation of NF-κB pathway.

Toxicity and repellency of patchouli oil and patchouli alcohol against Formosan subterranean termites Coptotermes formosanus Shiraki (Isoptera: Rhinotermitidae).[Pubmed: 14705881 ]

J Agric Food Chem. 2003 Jul 30;51(16):4585-8.

Patchouli oil obtained from Pogostemon cablin (Blanco) Benth and its main constituent, Patchouli alcohol, were tested for their repellency and toxicity against Formosan subterranean termites (Coptotermes formosanus Shiraki). Both were found to be toxic and repellent. Unusual tissue destruction was noted inside the exoskeleton of the termite after Patchouli alcohol was topically applied to the dorsum.

In vivo

Gastroprotective effect and mechanism of patchouli alcohol against ethanol, indomethacin and stress-induced ulcer in rats.[Pubmed: 25168850 ]

Chem Biol Interact. 2014 Oct 5;222:27-36.

Pogostemonis Herba is an important Chinese medicine widely used in the treatment of gastrointestinal dysfunction. Patchouli alcohol (PA), a tricyclic sesquiterpene, is the major active constituent of Pogostemonis Herba. This study aimed to investigate the possible anti-ulcerogenic potential of PA and the underlying mechanism against ethanol, indomethacin and water immersion restraint-induced gastric ulcers in rats.
METHODS AND RESULTS:
Gross and histological gastric lesions, biochemical and immunological parameters were taken into consideration. The gastric mucus content and the antisecretory activity were analyzed through pylorus ligature model in rats. Results indicated that oral administration with PA significantly reduced the ulcer areas induced by ethanol, indomethacin and water immersion restraint. PA pretreatment significantly promoted gastric prostaglandin E2 (PGE2) and non-protein sulfhydryl group (NP-SH) levels, upregulated the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) mRNA expression, and considerably boosted the gastric blood flow (GBF) and gastric mucus production in comparison with vehicle. In addition, PA modulated the levels of interleukin-6 (IL-6), interleukin-10 (IL-10) and tumor necrosis factor-α (TNF-α). The levels of glutathione (GSH), catalase (CAT) and malonaldehyde (MDA) were also restored by PA. However, the gastric secretion parameters (pH, volume of gastric juice and pepsin) did not show any significant alteration.
CONCLUSIONS:
These findings suggest that PA exhibited significant gastroprotective effects against gastric ulceration. The underlying mechanisms might involve the stimulation of COX-mediated PGE2, improvement of antioxidant and anti-inflammatory status, preservation of GBF and NP-SH, as well as boost of gastric mucus production.

Immunomodulatory Potential of Patchouli Alcohol Isolated from Pogostemon cablin (Blanco) Benth (Lamiaceae) in Mice[Reference: WebLink]

Trop. J.Pharm. Res., 2013, 12(4):559-65.

To isolate and purify Patchouli alcohol (PA), a tricyclic sesquiterpene constituent of Pogostemon cablin, and investigate its immunomodulatory potential in Kunming mice.
METHODS AND RESULTS:
PA was prepared from an ethanol aqueous extract of P. cablin by silica gel column chromatography, and further purified by crystallization using n-hexane. Purity was assessed by analytical gas chromatography (GC) and confirmation of chemical structure performed by Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). The effect of PA from Pogostemon cablin on immunological function was studied by macrophage phagocytosis, immune organ index, serum immunoglobulin level and delayed type hypersensitivity (DTH) in mice that were administered orally doses of 20, 40 and 80 mg/kg. The purity of PA was 99.3%. The oral administration of PA (40, or 80 mg/kg body weight) significantly increased the phagocytic index (p < 0.05), compared with prednisone acetate (PR) group. Administration of PA (80 mg/kg) boosted the production of circulating serum IgM (0.081 ± 0.010) and IgG (1.296 ± 0.120), while IgM and IgG in PR group was 0.069 ± 0.011 (p < 0.01) and 1.180 ± 0.070 (p < 0.01) respectively. However, PA (20 mg/kg) treatment elicited significant decrease in DTH induced by 2, 4-dinitro-chlorobenzene (DNCB) in mice (1.03 ± 0.40, p < 0.05), in comparison to DNCB-induced group (1.67 ± 0.84 mg).
CONCLUSIONS:
These results suggest that PA has significant immunomodulatory properties which probably act by activating mononuclear phagocytic system, augmenting humoral immune response while suppressing cellular immune response.

Protocol of Patchouli alcohol

Kinase Assay

Anti-inflammatory effect of patchouli alcohol isolated from Pogostemonis Herba in LPS-stimulated RAW264.7 macrophages.[Pubmed: 22977538]

Selective antibacterial activity of patchouli alcohol against Helicobacter pylori based on inhibition of urease.[Pubmed: 25243578]

Phytother Res. 2015 Jan;29(1):67-72.

The aim of this study is to evaluate the antibacterial activity and urease inhibitory effects of Patchouli alcohol (PA), the bioactive ingredient isolated from Pogostemonis Herba, which has been widely used for the treatment of gastrointestinal disorders.
METHODS AND RESULTS:
The activities of Patchouli alcohol against selected bacteria and fungi were determined by agar dilution method. It was demonstrated that Patchouli alcohol exhibited selective antibacterial activity against Helicobacter pylori, without influencing the major normal gastrointestinal bacteria. Noticeably, the antibacterial activity of Patchouli alcohol was superior to that of amoxicillin, with minimal inhibition concentration value of 78 µg/mL. On the other hand, Patchouli alcohol inhibited ureases from H.pylori and jack bean in concentration-dependent fashion with IC50 values of 2.67 ± 0.79 mM and 2.99 ± 0.41 mM, respectively. Lineweaver-Burk plots indicated that the type of inhibition was non-competitive against H.pylori urease whereas uncompetitive against jack bean urease. Reactivation of Patchouli alcohol-inactivated urease assay showed DL-dithiothreitol, the thiol reagent, synergistically inactivated urease with Patchouli alcohol instead of enzymatic activity recovery.
CONCLUSIONS:
In conclusion, the selective H.pylori antibacterial activity along with urease inhibitory potential of Patchouli alcohol could make it a possible drug candidate for the treatment of H.pylori infection.

Exp Ther Med. 2011 May;2(3):545-550.

Pogostemonis Herba has long been used in traditional Chinese medicine for the treatment of inflammation-related disorders. Patchouli alcohol (PA) isolated from Pogostemonis Herba is a tricyclic sesquiterpene that is known to exert a variety of pharmacological activities.
METHODS AND RESULTS:
The present study aimed to investigate the anti-inflammatory effect of PA on lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Pre-treatment with PA at concentrations of 10, 20 or 40 μM dose-dependently decreased the production of tumor necrosis factor (TNF)-α, interleukin (IL)-1β, IL-6, nitric oxide (NO) and prostaglandin E(2) in LPS-stimulated RAW264.7 cells. In addition, PA treatment also reversed the increased mRNA expression of TNF-α, IL-1β, IL-6, inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 caused by LPS in RAW264.7 cells.
CONCLUSIONS:
These results indicate that PA is an important anti-inflammatory constituent of Pogostemonis Herba and that its anti-inflammatory effect may be mediated, at least in part, by down-regulation of the mRNA expression of a panel of inflammatory mediators, such as TNF-α, IL-1β, IL-6, iNOS and COX-2.

Animal Research

Effects of topical application of patchouli alcohol on the UV-induced skin photoaging in mice.[Pubmed: 25033712]

Eur J Pharm Sci. 2014 Oct 15;63:113-23.

Ultraviolet (UV) irradiation, known to generate reactive oxygen species (ROS) excessively and elicit inflammatory response, is a potent inducer for skin photoaging. Overproduction of ROS in conjunction with the resulting inflammation stimulate the over-expression of matrix metalloproteinases (MMPs), which in turn causes degradation of extracellular matrix, leading finally to coarse wrinkling, dryness, and laxity of the skin.
METHODS AND RESULTS:
In this study, Patchouli alcohol (PA, C15H26O), an active chemical ingredient reputed for free radical scavenging and anti-inflammatory properties, was investigated for its anti-photoaging action using a mouse model whose dorsal skin was depilated. The dorsal skin areas of six-week-old mice were smeared with PA solution or vehicle, followed by UV irradiation for nine consecutive weeks. Protective effects of PA were evaluated macroscopically and histologically, as well as by assaying the antioxidant enzymes (SOD, GSH-Px) activities, the contents of inflammatory factors (IL-10, IL-6, TNF-α), and the levels of MMP-1 and MMP-3.
CONCLUSIONS:
Our findings amply demonstrated that PA significantly accelerated the recovery of the UV-induced skin lesions, evidently through anti-oxidant and anti-inflammatory action, as well as down-regulation of the MMP-1 and MMP-3 expression.

Patchouli alcohol Dilution Calculator

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Patchouli alcohol Molarity Calculator

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Preparing Stock Solutions of Patchouli alcohol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.4972 mL 22.4861 mL 44.9721 mL 89.9442 mL 112.4303 mL
5 mM 0.8994 mL 4.4972 mL 8.9944 mL 17.9888 mL 22.4861 mL
10 mM 0.4497 mL 2.2486 mL 4.4972 mL 8.9944 mL 11.243 mL
50 mM 0.0899 mL 0.4497 mL 0.8994 mL 1.7989 mL 2.2486 mL
100 mM 0.045 mL 0.2249 mL 0.4497 mL 0.8994 mL 1.1243 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 Patchouli alcohol

Gastroprotective effect and mechanism of patchouli alcohol against ethanol, indomethacin and stress-induced ulcer in rats.[Pubmed:25168850]

Chem Biol Interact. 2014 Oct 5;222:27-36.

Pogostemonis Herba is an important Chinese medicine widely used in the treatment of gastrointestinal dysfunction. Patchouli alcohol (PA), a tricyclic sesquiterpene, is the major active constituent of Pogostemonis Herba. This study aimed to investigate the possible anti-ulcerogenic potential of PA and the underlying mechanism against ethanol, indomethacin and water immersion restraint-induced gastric ulcers in rats. Gross and histological gastric lesions, biochemical and immunological parameters were taken into consideration. The gastric mucus content and the antisecretory activity were analyzed through pylorus ligature model in rats. Results indicated that oral administration with PA significantly reduced the ulcer areas induced by ethanol, indomethacin and water immersion restraint. PA pretreatment significantly promoted gastric prostaglandin E2 (PGE2) and non-protein sulfhydryl group (NP-SH) levels, upregulated the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) mRNA expression, and considerably boosted the gastric blood flow (GBF) and gastric mucus production in comparison with vehicle. In addition, PA modulated the levels of interleukin-6 (IL-6), interleukin-10 (IL-10) and tumor necrosis factor-alpha (TNF-alpha). The levels of glutathione (GSH), catalase (CAT) and malonaldehyde (MDA) were also restored by PA. However, the gastric secretion parameters (pH, volume of gastric juice and pepsin) did not show any significant alteration. These findings suggest that PA exhibited significant gastroprotective effects against gastric ulceration. The underlying mechanisms might involve the stimulation of COX-mediated PGE2, improvement of antioxidant and anti-inflammatory status, preservation of GBF and NP-SH, as well as boost of gastric mucus production.

Toxicity and repellency of patchouli oil and patchouli alcohol against Formosan subterranean termites Coptotermes formosanus Shiraki (Isoptera: Rhinotermitidae).[Pubmed:14705881]

J Agric Food Chem. 2003 Jul 30;51(16):4585-8.

Patchouli oil obtained from Pogostemon cablin (Blanco) Benth and its main constituent, Patchouli alcohol, were tested for their repellency and toxicity against Formosan subterranean termites (Coptotermes formosanus Shiraki). Both were found to be toxic and repellent. Unusual tissue destruction was noted inside the exoskeleton of the termite after Patchouli alcohol was topically applied to the dorsum.

Effects of topical application of patchouli alcohol on the UV-induced skin photoaging in mice.[Pubmed:25033712]

Eur J Pharm Sci. 2014 Oct 15;63:113-23.

Ultraviolet (UV) irradiation, known to generate reactive oxygen species (ROS) excessively and elicit inflammatory response, is a potent inducer for skin photoaging. Overproduction of ROS in conjunction with the resulting inflammation stimulate the over-expression of matrix metalloproteinases (MMPs), which in turn causes degradation of extracellular matrix, leading finally to coarse wrinkling, dryness, and laxity of the skin. In this study, Patchouli alcohol (PA, C15H26O), an active chemical ingredient reputed for free radical scavenging and anti-inflammatory properties, was investigated for its anti-photoaging action using a mouse model whose dorsal skin was depilated. The dorsal skin areas of six-week-old mice were smeared with PA solution or vehicle, followed by UV irradiation for nine consecutive weeks. Protective effects of PA were evaluated macroscopically and histologically, as well as by assaying the antioxidant enzymes (SOD, GSH-Px) activities, the contents of inflammatory factors (IL-10, IL-6, TNF-alpha), and the levels of MMP-1 and MMP-3. Our findings amply demonstrated that PA significantly accelerated the recovery of the UV-induced skin lesions, evidently through anti-oxidant and anti-inflammatory action, as well as down-regulation of the MMP-1 and MMP-3 expression.

Selective antibacterial activity of patchouli alcohol against Helicobacter pylori based on inhibition of urease.[Pubmed:25243578]

Phytother Res. 2015 Jan;29(1):67-72.

The aim of this study is to evaluate the antibacterial activity and urease inhibitory effects of Patchouli alcohol (PA), the bioactive ingredient isolated from Pogostemonis Herba, which has been widely used for the treatment of gastrointestinal disorders. The activities of PA against selected bacteria and fungi were determined by agar dilution method. It was demonstrated that PA exhibited selective antibacterial activity against Helicobacter pylori, without influencing the major normal gastrointestinal bacteria. Noticeably, the antibacterial activity of PA was superior to that of amoxicillin, with minimal inhibition concentration value of 78 microg/mL. On the other hand, PA inhibited ureases from H.pylori and jack bean in concentration-dependent fashion with IC50 values of 2.67 +/- 0.79 mM and 2.99 +/- 0.41 mM, respectively. Lineweaver-Burk plots indicated that the type of inhibition was non-competitive against H.pylori urease whereas uncompetitive against jack bean urease. Reactivation of PA-inactivated urease assay showed DL-dithiothreitol, the thiol reagent, synergistically inactivated urease with PA instead of enzymatic activity recovery. In conclusion, the selective H.pylori antibacterial activity along with urease inhibitory potential of PA could make it a possible drug candidate for the treatment of H.pylori infection.

Anti-inflammatory effect of patchouli alcohol isolated from Pogostemonis Herba in LPS-stimulated RAW264.7 macrophages.[Pubmed:22977538]

Exp Ther Med. 2011 May;2(3):545-550.

Pogostemonis Herba has long been used in traditional Chinese medicine for the treatment of inflammation-related disorders. Patchouli alcohol (PA) isolated from Pogostemonis Herba is a tricyclic sesquiterpene that is known to exert a variety of pharmacological activities. The present study aimed to investigate the anti-inflammatory effect of PA on lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Pre-treatment with PA at concentrations of 10, 20 or 40 muM dose-dependently decreased the production of tumor necrosis factor (TNF)-alpha, interleukin (IL)-1beta, IL-6, nitric oxide (NO) and prostaglandin E(2) in LPS-stimulated RAW264.7 cells. In addition, PA treatment also reversed the increased mRNA expression of TNF-alpha, IL-1beta, IL-6, inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 caused by LPS in RAW264.7 cells. These results indicate that PA is an important anti-inflammatory constituent of Pogostemonis Herba and that its anti-inflammatory effect may be mediated, at least in part, by down-regulation of the mRNA expression of a panel of inflammatory mediators, such as TNF-alpha, IL-1beta, IL-6, iNOS and COX-2.

Patchouli alcohol, an essential oil of Pogostemon cablin, exhibits anti-tumorigenic activity in human colorectal cancer cells.[Pubmed:23602914]

Int Immunopharmacol. 2013 Jun;16(2):184-90.

Patchouli alcohol (PA) is one of the important compounds isolated from the essential oil of Pogostemon cablin (patchouli). PA has neuroprotective, anti-influenza and anti-inflammatory activities. However, anti-cancer activity of PA has not been studied so far. We performed in vitro study to investigate whether PA affects proliferation and apoptosis of human colorectal cancer cells, and to define potential molecular mechanisms. PA suppressed cell growth and induced apoptosis in a dose-dependent manner in human colorectal cancer cells (HCT116, SW480). In addition, PA decreased cell growth in MCF7, BxPC3, PC3, and HUVEC cells. Exposure of PA to HCT116 and SW480 cells activated p21 expression and suppressed the expressions of cyclin D1 and cyclin-dependent kinase 4 (CDK4) in a dose-dependent manner. In addition, PA attenuated the expressions of HDAC2 (histone deacetylase 2) and c-myc, and HDAC enzyme activity. We also observed that PA induced the transcriptional activity of NF-kappaB through an increase of nuclear translocation of p65. These findings suggest that PA exerts an anti-cancer activity by decreasing cell growth and increasing apoptosis in human colorectal cancer cells. The proposed mechanisms include the inhibition of HDAC2 expression and HDAC enzyme activity, and subsequent downregulation of c-myc and activation of NF-kappaB pathway.

Description

Patchouli alcohol is a natural tricyclic sesquiterpene extracted from Pogostemon cablin (Blanco) Benth, and exhibits anti-Helicobacter pylori and anti-inflammatory properties.

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