MedKoo Cat#: 333059 | Name: Norbergenin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Norbergenin, also known as Demethylbergenin, is the O-demethyl derivative of bergenin, the main component of Mallotus japonicus, has been found to show moderate antioxidant activity (IC(50) 13 microM in DPPH radical scavenging; 32 microM in superoxide anion scavenging).

Chemical Structure

Norbergenin
Norbergenin
CAS#79595-97-4

Theoretical Analysis

MedKoo Cat#: 333059

Name: Norbergenin

CAS#: 79595-97-4

Chemical Formula: C13H14O9

Exact Mass: 314.0638

Molecular Weight: 314.25

Elemental Analysis: C, 49.69; H, 4.49; O, 45.82

Price and Availability

Size Price Availability Quantity
50mg USD 1,350.00 2 Weeks
100mg USD 1,950.00 2 Weeks
200mg USD 2,950.00 2 Weeks
500mg USD 3,950.00 2 Weeks
1g USD 5,950.00 2 Weeks
2g USD 8,950.00 2 Weeks
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Related CAS #
No Data
Synonym
Norbergenin; Demethylbergenin,
IUPAC/Chemical Name
Pyrano(3,2-c)(2)benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,9,10-pentahydroxy-2-(hydroxymethyl)-, (2R-(2alpha,3beta,4alpha,4aalpha,10bbeta))-
InChi Key
GDYGAIKPBLFCKR-OIPGZRGRSA-N
InChi Code
InChI=1S/C13H14O9/c14-2-5-8(17)10(19)12-11(21-5)6-3(13(20)22-12)1-4(15)7(16)9(6)18/h1,5,8,10-12,14-19H,2H2/t5-,8-,10+,11+,12-/m1/s1
SMILES Code
O=C1C2=CC(O)=C(O)C(O)=C2[C@@]3([H])[C@]([C@@H](O)[C@H](O)[C@@H](CO)O3)([H])O1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Norbergenin, the O-demethyl derivative of bergenin, shows moderate antioxidant activity (IC50 13 μM in DPPH radical scavenging; 32 μM in superoxide anion scavenging).
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 125.0 397.78
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 314.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Suzuki S, Okuse Y, Kawase M, Takiguchi M, Fukuyama Y, Takahashi H, Sato M. A norbergenin derivative inhibits neuronal cell damage induced by tunicamycin. Biol Pharm Bull. 2006 Jul;29(7):1335-8. doi: 10.1248/bpb.29.1335. PMID: 16819164. 2: Akak CM, Nkengfack AE, Tu PF. Norbergenin derivatives from Diospyros crassiflora (Ebenaceae). Nat Prod Commun. 2013 Nov;8(11):1575-8. PMID: 24427945. 3: Nazir N, Koul S, Qurishi MA, Taneja SC, Ahmad SF, Bani S, Qazi GN. Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis--a flow cytometric study. J Ethnopharmacol. 2007 Jun 13;112(2):401-5. doi: 10.1016/j.jep.2007.02.023. Epub 2007 Feb 28. PMID: 17408893. 4: Zhang YH, Fang LH, Lee MK, Ku BS. In vitro inhibitory effects of bergenin and norbergenin on bovine adrenal tyrosine hydroxylase. Phytother Res. 2003 Sep;17(8):967-9. doi: 10.1002/ptr.1292. PMID: 13680837. 5: Tangmouo JG, Ho R, Matheeussen A, Lannang AM, Komguem J, Messi BB, Maes L, Hostettmann K. Antimalarial activity of extract and norbergenin derivatives from the stem bark of Diospyros sanza-minika A. Chevalier (Ebenaceae). Phytother Res. 2010 Nov;24(11):1676-9. doi: 10.1002/ptr.3192. PMID: 21031627. 6: Takahashi H, Kosaka M, Watanabe Y, Nakade K, Fukuyama Y. Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity. Bioorg Med Chem. 2003 Apr 17;11(8):1781-8. doi: 10.1016/s0968-0896(02)00666-1. PMID: 12659764. 7: Tenuta MC, Deguin B, Loizzo MR, Dugay A, Acquaviva R, Malfa GA, Bonesi M, Bouzidi C, Tundis R. Contribution of Flavonoids and Iridoids to the Hypoglycaemic, Antioxidant, and Nitric Oxide (NO) Inhibitory Activities of Arbutus unedo L. Antioxidants (Basel). 2020 Feb 22;9(2):184. doi: 10.3390/antiox9020184. PMID: 32098404; PMCID: PMC7071084. 8: Goel RK, Maiti RN, Manickam M, Ray AB. Antiulcer activity of naturally occurring pyrano-coumarin and isocoumarins and their effect on prostanoid synthesis using human colonic mucosa. Indian J Exp Biol. 1997 Oct;35(10):1080-3. PMID: 9475044. 9: Sumino M, Sekine T, Ruangrungsi N, Igarashi K, Ikegami F. Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata. Chem Pharm Bull (Tokyo). 2002 Nov;50(11):1484-7. doi: 10.1248/cpb.50.1484. PMID: 12419914. 10: Hendrychová H, Tůmová L. Rod Bergenia - obsahové látky a biologická aktivita [Bergenia genus - content matters and biological activity]. Ceska Slov Farm. 2012 Oct;61(5):203-9. Czech. PMID: 23256653. 11: Li YF, Hu LH, Lou FC, Li J, Shen Q. PTP1B inhibitors from Ardisia japonica. J Asian Nat Prod Res. 2005 Feb;7(1):13-8. doi: 10.1080/10286020310001596033. PMID: 15621596. 12: Zamarrud, Ali I, Hussain H, Ahmad VU, Qaiser M, Amyn A, Mohammad FV. Two new antioxidant bergenin derivatives from the stem of Rivea hypocrateriformis. Fitoterapia. 2011 Jun;82(4):722-5. doi: 10.1016/j.fitote.2011.03.002. Epub 2011 Mar 22. PMID: 21406219. 13: Liu D, Yang P, Zhang YQ. Water-soluble extract of Saxifraga stolonifera has anti-tumor effects on Lewis lung carcinoma-bearing mice. Bioorg Med Chem Lett. 2016 Oct 1;26(19):4671-4678. doi: 10.1016/j.bmcl.2016.08.051. Epub 2016 Aug 20. PMID: 27575479. 14: Van NT, Vien TA, Van Kiem P, Van Minh C, Nhiem NX, Long PQ, Anh LT, Kim N, Park S, Kim SH. Chemical components from the leaves of Ardisia insularis and their cytotoxic activity. Arch Pharm Res. 2015 Nov;38(11):1926-31. doi: 10.1007/s12272-015-0591-x. Epub 2015 Mar 21. PMID: 25794927. 15: Bajracharya GB. Diversity, pharmacology and synthesis of bergenin and its derivatives: potential materials for therapeutic usages. Fitoterapia. 2015 Mar;101:133-52. doi: 10.1016/j.fitote.2015.01.001. Epub 2015 Jan 14. PMID: 25596093. 16: Piacente S, Pizza C, De Tommasi N, Mahmood N. Constituents of Ardisia japonica and their in vitro anti-HIV activity. J Nat Prod. 1996 Jun;59(6):565-9. doi: 10.1021/np960074h. PMID: 8786362. 17: Newell AM, Yousef GG, Lila MA, Ramírez-Mares MV, de Mejia EG. Comparative in vitro bioactivities of tea extracts from six species of Ardisia and their effect on growth inhibition of HepG2 cells. J Ethnopharmacol. 2010 Aug 9;130(3):536-44. doi: 10.1016/j.jep.2010.05.051. Epub 2010 Jun 2. PMID: 20561930. 18: Liu J, Li GQ, Wu X, Li YL, Wang GC. [Chemical constituents from Glechoma longituba]. Zhongguo Zhong Yao Za Zhi. 2014 Feb;39(4):695-8. Chinese. PMID: 25204149. 19: Han L, Ni MY. [Studies on the chemical constituents of Ardisia crenata Sims]. Zhongguo Zhong Yao Za Zhi. 1989 Dec;14(12):737-9, 762-3. Chinese. PMID: 2635600. 20: Kashima Y, Miyazawa M. Synthesis, antioxidant capacity, and structure- activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition. Bioorg Med Chem Lett. 2013 Dec 15;23(24):6580-4. doi: 10.1016/j.bmcl.2013.10.066. Epub 2013 Nov 7. PMID: 24268551.