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MedKoo Cat#: 461550 | Name: Rubrolone

Description:

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

Rubrolone is a tropolonoid natural product with a unique carbon skeleton.

Chemical Structure

Rubrolone
Rubrolone
CAS#65445-21-8

Theoretical Analysis

MedKoo Cat#: 461550

Name: Rubrolone

CAS#: 65445-21-8

Chemical Formula: C23H23NO8

Exact Mass: 441.1424

Molecular Weight: 441.43

Elemental Analysis: C, 62.58; H, 5.25; N, 3.17; O, 28.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Rubrolone; Ro 21-1660/002; Ro-21-1660/002; Ro21-1660/002;
IUPAC/Chemical Name
(2R,3R,4S,4aR,13aS)-3,4,4a,5-tetrahydroxy-2,10-dimethyl-8-propyl-3,4,4a,13a-tetrahydro-2H-pyrano[3'',2'':4',5']furo[3',2':6,7]azuleno[2,1-c]pyridine-7,12-dione
InChi Key
UURMXICTBNVMJV-TUMZLJIFSA-N
InChi Code
InChI=1S/C23H23NO8/c1-4-5-12-15-10(6-8(2)24-12)14-11(18(15)27)7-13(25)16-20(19(14)28)32-22-23(16,30)21(29)17(26)9(3)31-22/h6-7,9,17,21-22,25-26,29-30H,4-5H2,1-3H3/t9-,17+,21+,22+,23-/m1/s1
SMILES Code
O=C(C1=C2C=C(C)N=C1CCC)C(C=C(O)C3=C4O[C@@]5([H])[C@]3(O)[C@@H](O)[C@@H](O)[C@@H](C)O5)=C2C4=O
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 441.43 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
1: Yan Y, Yang J, Yu Z, Yu M, Ma YT, Wang L, Su C, Luo J, Horsman GP, Huang SX. Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids. Nat Commun. 2016 Oct 7;7:13083. doi: 10.1038/ncomms13083. PubMed PMID: 27713400; PubMed Central PMCID: PMC5059770. 2: Yan Y, Ma YT, Yang J, Horsman GP, Luo D, Ji X, Huang SX. Tropolone Ring Construction in the Biosynthesis of Rubrolone B, a Cationic Tropolone Alkaloid from Endophytic Streptomyces. Org Lett. 2016 Mar 18;18(6):1254-7. doi: 10.1021/acs.orglett.6b00074. Epub 2016 Feb 29. PubMed PMID: 26926531. 3: Schüep W, Blount JF, Williams TH, Stempel A. Production of a novel red pigment, rubrolone, by Streptomyces echinoruber Sp. Nov. II. Chemistry and structure elucidation. J Antibiot (Tokyo). 1978 Dec;31(12):1226-32. PubMed PMID: 738966. 4: Palleroni NJ, Reichelt KE, Mueller D, Epps R, Tabenkin B, Bull DN, Schüep W, Berger J. Production of a novel red pigment, rubrolone, by Streptomyces echinoruber sp. nov. I. Taxonomy, fermentation and partial purification. J Antibiot (Tokyo). 1978 Dec;31(12):1218-25. PubMed PMID: 738965.