6-beta-Hydroxyhyoscyamine | CAS:55869-99-3

6-beta-Hydroxyhyoscyamine

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Description:

6-beta-Hydroxyhyoscyamine and 7 beta-hydroxyhyoscyamine exhibit similar affinities at the muscarinic receptor as scopolamine and atropine.

Targets:

AChR

In vitro:

Pharmazie. 1995 Jul;50(7):493-5.

Binding of tropane alkaloids to nicotinic and muscarinic acetylcholine receptors.[Pubmed: 7675895]

METHODS AND RESULTS:
Fourteen tropane and related alkaloids were analyzed for their affinity for nicotinic and/or muscarinic acetylcholine receptors. The biogenetic intermediates littorine, 6-beta-Hydroxyhyoscyamine, 7 beta-hydroxyhyoscyamine exhibit similar affinities at the muscarinic receptor as scopolamine and atropine.
CONCLUSIONS:
The quarternary derivatives N-methylatropine and N-methylscopolamine show the highest binding with IC50 values of less than 100 pM and 300 pM, respectively. The tropane alkaloids (including cocaine) also bind to the nicotinic acetylcholine receptor, albeit with much lower affinities.

6-beta-Hydroxyhyoscyamine Description

Source:	The roots of Anisodus tanguticus
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

More...

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
IF=36.216(2019)

PMID: 29328914

Cell Metab. 2020 Mar 3;31(3):534-548.e5.
doi: 10.1016/j.cmet.2020.01.002.
IF=22.415(2019)

PMID: 32004475

Mol Cell. 2017 Nov 16;68(4):673-685.e6.
doi: 10.1016/j.molcel.2017.10.022.
IF=14.548(2019)

PMID: 29149595

ACS Nano. 2018 Apr 24;12(4): 3385-3396.
doi: 10.1021/acsnano.7b08969.
IF=13.903(2019)

PMID: 29553709

Nature Plants. 2016 Dec 22;3: 16206.
doi: 10.1038/nplants.2016.205.
IF=13.297(2019)

PMID: 28005066

Sci Adv. 2018 Oct 24;4(10): eaat6994.
doi: 10.1126/sciadv.aat6994.
IF=12.804(2019)

PMID: 30417089

Structure Identification:

Planta Med. 2005 Mar;71(3):249-53.

Molecular cloning, expression and characterization of hyoscyamine 6beta-hydroxylase from hairy roots of Anisodus tanguticus.[Pubmed: 15770546]

METHODS AND RESULTS:
Anisodus tanguticus, one of the indigenous Chinese ethnological medicinal plants of the Solanaceae, produces anticholinergic alkaloids such as hyoscyamine, 6 beta-hydroxyhyoscyamine and scopolamine. Hyoscyamine 6 beta-hydroxylase (H6H), a key enzyme in the biosynthetic pathway of scopolamine, catalyzes the hydroxylation of hyoscyamine and epoxide formation from 6-beta-Hydroxyhyoscyamine to generate scopolamine. A full-length cDNA of H6H has been isolated from A. tanguticus hairy roots. Nucleotide sequence analysis of the cloned cDNA revealed an open reading frame of 1035 bp encoding 344 amino acids with high homology to other known H6Hs. The equivalent amino acid sequence shows a typical motif of 2-oxoglutarate-dependent dioxygenase. The A. tanguticus H6H was expressed in Escherichia coli and purified for enzyme function analysis.
CONCLUSIONS:
This study characterized the recombinant AtH6H and showed it could generate scopolamine from hyoscyamine.

Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku. 2002;(120):85-8.

Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides.[Pubmed: 12638187]

METHODS AND RESULTS:
Adventitious and hairy root cultures of Physochlaina physaloides were established. These roots grew well and produced high amounts of tropane alkaloids (particularly hyoscyamine and 6-beta-Hydroxyhyoscyamine) in auxin-free culture medium. The effects of basal media and temperature on the growth and alkaloid production of these roots were investigated.
CONCLUSIONS:
Both root cultures produced highest amount of tropane alkaloids in B5 medium though the optimum temperature for hairy roots were lower than that for adventitious roots.

CAS No.	55869-99-3	Price
Catalog No.	CFN00198	Purity	>=98%
Molecular Weight	305.37	Type of Compound	Alkaloids
Formula	C₁₇H₂₃NO₄	Physical Description	Powder
Download	Manual COA MSDS SDF	Similar structural	Comparison (Web) (SDF)

Product Name	6-beta-Hydroxyhyoscyamine
CAS No.:	55869-99-3
Catalog No.:	CFN00198
Molecular Formula:	C₁₇H₂₃NO₄
Molecular Weight:	305.37 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Targets:	AChR
Source:	The roots of Anisodus tanguticus
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Precursors Compound Library Alkaloids Compound Library AChR Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.2747 mL	16.3736 mL	32.7472 mL	65.4943 mL	81.8679 mL
5 mM	0.6549 mL	3.2747 mL	6.5494 mL	13.0989 mL	16.3736 mL
10 mM	0.3275 mL	1.6374 mL	3.2747 mL	6.5494 mL	8.1868 mL
50 mM	0.0655 mL	0.3275 mL	0.6549 mL	1.3099 mL	1.6374 mL
100 mM	0.0327 mL	0.1637 mL	0.3275 mL	0.6549 mL	0.8187 mL

CFN00186	Convolvine	537-30-4	291.34	C₁₆H₂₁NO₄
CFN00187	Convolamine	500-56-1	305.37	C₁₇H₂₃NO₄
CFN00188	Darlingine	58471-10-6	219.28	C₁₃H₁₇NO₂
CFN00189	Ecgonine	481-37-8	185.22	C₉H₁₅NO₃
CFN00190	Methylecgonine	7143-09-1	199.25	C₁₀H₁₇NO₃
CFN00191	Benzoylecgonine	519-09-5	289.33	C₁₆H₁₉NO₄
CFN00192	Cinnamoylcocaine	521-67-5	329.4	C₁₉H₂₃NO₄
CFN00196	Knightinol	77053-06-6	289.37	C₁₇H₂₃NO₃
CFN00197	Acetylknightinol	77053-07-7	331.41	C₁₉H₂₅NO₄
CFN00198	6-beta-Hydroxyhyoscyamine	55869-99-3	305.37	C₁₇H₂₃NO₄