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Agatharesinol

CAS# 7288-11-1

Agatharesinol

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Chemical structure

Agatharesinol

3D structure

Chemical Properties of Agatharesinol

Cas No. 7288-11-1 SDF Download SDF
PubChem ID 15558522 Appearance Powder
Formula C17H18O4 M.Wt 286.33
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E,2S,3S)-3,5-bis(4-hydroxyphenyl)pent-4-ene-1,2-diol
SMILES C1=CC(=CC=C1C=CC(C2=CC=C(C=C2)O)C(CO)O)O
Standard InChIKey DVUXXXYVVWRAIA-UDEVJOAWSA-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.
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 Agatharesinol

The barks of Cryptomeria japonica

Biological Activity of Agatharesinol

Description1. Agatharesinol is localized in the ray parenchyma cells in Sugi heartwood, and differences between the chemical structure of the contents of ray and axial parenchyma cells were also suggested.

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Preparing Stock Solutions of Agatharesinol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4925 mL 17.4624 mL 34.9247 mL 69.8495 mL 87.3118 mL
5 mM 0.6985 mL 3.4925 mL 6.9849 mL 13.9699 mL 17.4624 mL
10 mM 0.3492 mL 1.7462 mL 3.4925 mL 6.9849 mL 8.7312 mL
50 mM 0.0698 mL 0.3492 mL 0.6985 mL 1.397 mL 1.7462 mL
100 mM 0.0349 mL 0.1746 mL 0.3492 mL 0.6985 mL 0.8731 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 Agatharesinol

Immunohistochemical localization of agatharesinol, a heartwood norlignan, in Cryptomeria japonica.[Pubmed:12052511]

Phytochemistry. 2002 Jul;60(5):461-6.

Localization of a heartwood norlignan, Agatharesinol, in Sugi (Japanese cedar, Cryptomeria japonica D. Don, Taxodiaceae) was investigated by immunohistochemistry. Immuno light microscopy showed that the contents of ray parenchyma cells were immunostained in heartwood but not in sapwood. The staining of the heartwood tissue was competitively inhibited by Agatharesinol but not by other Sugi heartwood extractives, and was, furthermore, markedly reduced by pre-extraction of the tissue with MeOH. These results indicated that the staining can be ascribed to the immunolabeling of Agatharesinol in situ. The accumulations over the inner surface of some tracheid cell walls adjacent to the ray parenchyma cells were also immunolabeled, while the contents in axial parenchyma cells were not. In conclusion, Agatharesinol was localized in the ray parenchyma cells in Sugi heartwood, and differences between the chemical structure of the contents of ray and axial parenchyma cells were also suggested.

Evidence for involvement of the phenylpropanoid pathway in the biosynthesis of the norlignan agatharesinol.[Pubmed:16473652]

J Plant Physiol. 2006 Mar;163(5):483-7.

In order to study the biosynthesis of Agatharesinol, a norlignan, l-phenylalanine-[ring-2,3,4,5,6-2H] and trans-cinnamic acid-[ring-13C6] were administered to fresh sapwood sticks of Cryptomeria japonica (sugi, Japanese cedar), that is, the labeled precursors were allowed to be absorbed through the tangential section of the wood sticks. The wood sticks were then maintained in high humidity desiccators for approximately 20 d after which ethyl acetate (EtOAc) extracts of the wood sticks were analyzed by gas chromatography-mass spectrometry (GC-MS). Native Agatharesinol (trimethylsilylated) produces an m/z 369 ion and an m/z 484 ion that are characteristic of its structure. Agatharesinol formed in the sapwood sticks treated with the deuterium-labeled l-phenylalanine generated both of these ions together with m/z 373 and 377 ions (m/z 369+4 and +8, respectively), and also m/z 488 and 492 ions (m/z 484+4 and +8, respectively). Generation of m/z 373 and 488 ions is attributed to the substitution by deuterium of the four hydrogen atoms of either of the p-hydroxyphenyl rings of Agatharesinol, and that of m/z 377 and 492 ions is attributed to the substitution by deuterium of the eight hydrogen atoms of both p-hydroxyphenyl rings. In the administration of the 13C-labeled trans-cinnamic acid, m/z 375 and 381 ions (m/z 369+6 and +12, respectively), and also m/z 490 and 496 ions (m/z 484+6 and +12, respectively) were found, indicating that either aromatic ring or both aromatic rings of Agatharesinol were 13C-labeled. Consequently, assimilation of the labeled precursors into Agatharesinol was clearly detected, and an experimental procedure for studies on the biosynthesis was developed.

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