51348-66-4

Basic information

• Product Name: (+/-)-Tulipalin B
• CAS NO: 51348-66-4
• Molecular Weight: 114.101
• Mol File: 51348-66-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (+/-)-Tulipalin B(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-Tulipalin B(51348-66-4)
• EPA Substance Registry System: (+/-)-Tulipalin B(51348-66-4)

Safety Data

• Hazardous Substances Data: 51348-66-4(Hazardous Substances Data)

Usage

Description

(+/-)-Tulipalin B is a toxic polyphenolic chemical compound found in the bulbs of tulip plants (Tulipa spp). It is known for its potent skin irritant properties, causing dermatitis in humans upon contact with the skin, and can lead to allergic reactions such as redness, itching, and blistering, especially in individuals with sensitive skin or those allergic to tulips.

Upstream product

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Relevant articles and documents

A NEW TEMPLATE of MITSUNOBU ACYLATE CLEAVABLE in NONALKALINE CONDITIONS

The Mitsunobu inversion is one of the reliable methods for stereospecific substitution of chiral alcohols, but its deacylation step has limited the substrate scope. Here, we propose a new template of the Mitsunobu acylate that can be deacylated in non-alkaline treatments. The 3,4-dihydroxy-2-methylenebutanoate was selected as a template structure, and its acetonide- or bisTBS derivatives were synthesized. The latter especially showed excellent inversion efficiency (up to >99% ee) and good elimination performance for a series of secondary alcohols in near-neutral conditions. The results demonstrated the applicability of the new template for the substrates labile in alkaline conditions, such as a-hydroxyesters.

Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA

The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity relationships of various derivatives. The inhibition of MurA can be related to antibacterial activity, and MurA is probably one of the relevant molecular targets of the tulipaline derivatives. MurA inhibition by this class of compounds depends on the presence of the substrate UNAG, which indicates non-covalent suicide inhibition as observed previously for cnicin. With respect to selectivity, however, the reactivity against arbitrary sulfhydryl groups, such as in glutathione, could not yet be sufficiently separated from MurA inhibition in the present dataset.

Synthesis of tulipalin B and 1-O-methyl-6-tuliposide B

Toward the total synthesis of 6-tuliposide B, facile synthesis of tulipalin B and 1-O-methyl-6-tuliposide B (Methyl 6-0-((S)-3′,4′-dihydroxy-2′-methylenebutanoyl)-β-D-glucopyranoside) has been achieved.