Ajugamarin chlorohydrinCAS# 85447-27-4 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 85447-27-4 | SDF | Download SDF |
| PubChem ID | 102004685 | Appearance | Powder |
| Formula | C29H41ClO10 | M.Wt | 585.1 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [(4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-4-(chloromethyl)-4-hydroxy-8-[(2R)-2-hydroxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] (E)-2-methylbut-2-enoate | ||
| SMILES | CC=C(C)C(=O)OC1CCC(C2(C1C(C(CC2OC(=O)C)C)(C)CC(C3=CC(=O)OC3)O)COC(=O)C)(CCl)O | ||
| Standard InChIKey | CWWDVANTGWQWKM-QQFGKRSBSA-N | ||
| 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. |
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| 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. |
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| 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. | ||
| Structure Identification | CHEMICAL & PHARMACEUTICAL BULLETIN, 1983, 31(7):2192-2199.The Chemical Constituents of Ajuga Plants. I. neo-Clerodanes from the Leaves of Ajuga nipponensis MAKINO.[Reference: WebLink]
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Ajugamarin chlorohydrin Dilution Calculator
Ajugamarin chlorohydrin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.7091 mL | 8.5455 mL | 17.0911 mL | 34.1822 mL | 42.7277 mL |
| 5 mM | 0.3418 mL | 1.7091 mL | 3.4182 mL | 6.8364 mL | 8.5455 mL |
| 10 mM | 0.1709 mL | 0.8546 mL | 1.7091 mL | 3.4182 mL | 4.2728 mL |
| 50 mM | 0.0342 mL | 0.1709 mL | 0.3418 mL | 0.6836 mL | 0.8546 mL |
| 100 mM | 0.0171 mL | 0.0855 mL | 0.1709 mL | 0.3418 mL | 0.4273 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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(S)-alpha-chlorohydrin inhibits protein tyrosine phosphorylation through blocking cyclic AMP - protein kinase A pathway in spermatozoa.[Pubmed:22916194]
PLoS One. 2012;7(8):e43004.
alpha-Chlorohydrin is a common contaminant in food. Its (S)-isomer, (S)-alpha-chlorohydrin (SACH), is known for causing infertility in animals by inhibiting glycolysis of spermatozoa. The aim of present work was to examine the relationship between SACH and protein tyrosine phosphorylation (PTP), which plays a critical role in regulating mammalian sperm capacitation. In vitro exposure of SACH 50 microM to isolated rat epididymal sperm inhibited PTP. Sperm-specific glyceraldehyde 3-phosphate dehydrogenase (GAPDS) activities, the intracellular adenosine 5'-triphosphate (ATP) levels, 3'-5'-cyclic adenosine monophosphate (cAMP) levels and phosphorylation of protein kinase A (PKA) substrates in rat sperm were diminished dramatically, indicating that both glycolysis and the cAMP/PKA signaling pathway were impaired by SACH. The inhibition of both PTP and phosphorylation of PKA substrates by SACH could be restored by addition of cAMP analog dibutyryl-cAMP (dbcAMP) and phosphodiesterase inhibitor 3-isobutyl-1-methylxanthine (IBMX). Moreover, addition of glycerol protected glycolysis, ATP levels, phosphorylation of PKA substrates and PTP against the influence of SACH. These results suggested SACH inhibited PTP through blocking cAMP/PKA pathway in sperm, and PTP inhibition may play a role in infertility associated with SACH.
Ameliorative effects of pine bark extract on spermatotoxicity by alpha-chlorohydrin in rats.[Pubmed:23788506]
Phytother Res. 2014 Mar;28(3):451-7.
We investigated the protective effects of pine bark extract (Pycnogenol(R), PYC, Horphag Research Ltd., Route de Belis, France) against alpha-chlorohydrin (ACH)-induced spermatotoxicity in rats. Rats were orally administered ACH (30 mg/kg/day) with or without PYC (20 mg/kg/day) for 7 days. Administration of ACH significantly decreased sperm motility. alpha-Chlorohydrin also caused histopathological alterations and apoptotic changes in caput epididymides. An increased malondialdehyde concentration and decreased glutathione content, as well as catalase and glutathione peroxidase activities were also found. In contrast, PYC treatment significantly prevented ACH-induced spermatotoxicity, including decreased sperm motility, histopathological lesions, and apoptotic changes in the caput epididymis. Pycnogenol(R) also had an antioxidant benefit by decreasing malondialdehyde and increasing levels of the antioxidant glutathione and the activities of the antioxidant enzymes catalase and peroxidase in epididymal tissues. These results indicate that PYC treatment attenuated ACH-induced spermatotoxicity through antioxidant and antiapoptotic effects.
Spermatotoxic effects of alpha-chlorohydrin in rats.[Pubmed:22474469]
Lab Anim Res. 2012 Mar;28(1):11-6.
This study was conducted to investigate the potential effects of alpha-chlorohydrin (ACH) on epididymal function and antioxidant system in male rats. The test chemical was administered to male rats by gavage at doses of 0, 3, 10, and 30 mg/kg/day for 7 days. Twenty-four male rats were randomly assigned to four experimental groups, with six rats in each group. Spermatotoxicity was assessed by measurement of reproductive organ weight, testicular sperm head count, epididymal sperm motility and morphology, histopathologic examination, and oxidative damage analysis in rats. At 30 mg/kg/day, an increase in the incidence of clinical signs, epididymis weight, and gross necropsy findings of the epididymis, a decrease in the sperm motility, and an increased incidence of histopathological changes of the epididymis were observed in a dose-dependent manner. At 10 mg/kg/day, an increased incidence of clinical signs and histopathological changes and decreased sperm motility were observed. In the oxidative damage analysis, an increase in the malondialdehyde concentration and a decrease in the glutathione content and glutathione peroxidase and catalase activities in the epididymal tissue were detected at >/=3 mg/kg/day. The results show that graded doses of ACH elicit depletion of the antioxidant defense system and that the spermatotoxicity of ACH may be due to the induction of oxidative stress.
Evaluating the anti-fertility potential of alpha-chlorohydrin on testis and spermatozoa in the adult male wild Indian house rat (Rattus rattus).[Pubmed:21967454]
J Environ Pathol Toxicol Oncol. 2011;30(2):93-102.
To examine the effects of alpha-chlorohydrin on testis and cauda epididymis in the male house rat (Rattus rattus), 24 adult male rats were segregated into two groups. Group I rats were force-fed daily by intragastric intubation with alpha-chlorohydrin at a single dose of 1.0 mg/100 g body weight/d for 5, 15, and 45 days. Another group was fed with distilled water, which served as the control. The treated male rats were paired with 24 adult proestrus female rats for 5 days after the last oral treatment and fertility was tested. At the end of the experiments, all of the male rats were weighed and killed by cervical dislocation. The right testes were removed, weighed, and processed for ultrastructural changes of spermatozoa from the cauda epididymis and testis under scanning electron microscopy (SEM) and transmission electron microscopy (TEM). The seminiferous tubular area, nuclear diameter of the Sertoli and Leydig cells, percentage of spermatogonia, primary spermatocytes, secondary spermatocytes, spermatids, spermatozoa, and Sertoli cells in each group were compared morphometrically. Our results showed that the percentages of primary spermatocytes steadily increased from 5 to 15 days, but primary and secondary spermatocytes decreased significantly at 45 days. There was a steady decline in the percentages of spermatozoa and spermatids at all fixation intervals in the treated animals, but the percentages of spermatogonia and Sertoli cells increased significantly at 15 and 45 days. Seminiferous tubular areas, nuclear diameter of Leydig and Sertoli cells, and fertility rates were reduced after 45 days of treatment. SEM and TEM studies revealed severe morphological abnormalities in the spermatozoa, including deglutination of the acrosomal part, loss of head capsules, and fragmentation of tail fibrils. There was an enhanced anti-fertility effect and a lower number of implantation sites in the rats treated for 5 days. Our results validate alpha-chlorohydrin as a successful anti-fertility agent that prevents spermatogenesis.
[Inhibitory effect of (S)-chlorohydrin on rat sperm motility and hyperactivation].[Pubmed:23213680]
Wei Sheng Yan Jiu. 2012 Sep;41(5):704-9.
OBJECTIVE: To investigate the effects of (S)-alpha-chlorohydrin (SACH) on rat epididymal sperm motility and hyperactivation and explore the mechanisms of the effects. METHODS: 20 adult male Sprague-Dawley rats were divided randomly into 4 groups and dosed orally with 0, 2.5, 5.0 and 10 mg/kg BW SACH respectively for 52 days. After the cauda epididymal sperm were incubated under a capacitating condition for 5 h, sperm motility and hyperactivation parameters were obtained by computer-assisted sperm analysis (CASA), and sperm-specific glyceraldehyde 3-phosphate dehydrogenase (GAPDS) activity, adenosine triphosphate (ATP) and cyclic adenosine monophosphate (cAMP) were assayed. The protecting effect of pentoxifylline (PTF) against SACH was aslo tested. RESULTS: The sperm from the SACH-treated rats treated showed significant decreases in curvilinear velocity (VCL), average path velocity (VAP), straight line velocity (VSL) and amplitude of lateral head movement (ALH) (P < 0.01 of all), and an increase in linearity (LIN) (P < 0.01). The SACH-treated rats had much less sperm population with VCL > or = 400 microm/s or LIN < or = 20% than that of the control (P < 0.05 and P < 0.01, respectively), indicating that SACH diminished hyperactivation of rat sperm. GAPDS activities were inhibited by SACH, and decreasing trends of ATP and cAMP levels were observed. PTF rescued the cAMP level which was depressed by SACH, and alleviated in part the inhibition of sperm motility and hyperactivation. CONCLUSION: SACH impaired the motility and hyperactivation of rat sperm, which might result from the inhibition of GAPDS by SACH and subsequent defects of ATP and cAMP.
