14-Acetylandrographolide

Srinivasa Rao Jada; Katherine McMillan; Ahmad S. Hamzah; Mohammad S. Saad; Nordin H. Lajis; Malcolm F G Stevens; Carl H. Schwalbe; Johnson Stanslas

doi:10.1007/s10870-005-9004-1

14-Acetylandrographolide

Srinivasa Rao Jada, Katherine McMillan, Ahmad S. Hamzah, Mohammad S. Saad, Nordin H. Lajis, Malcolm F G Stevens, Carl H. Schwalbe, Johnson Stanslas^*

^*Corresponding author for this work

Aston Pharmacy School

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a- dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C ₂₂H ₃₂O ₆, was synthesised from andrographolide. It crystallizes in the orthorhombic system with a = 7.4219(12), b = 11.8411(10), c = 23.777(4) Å in space group P2 ₁2 ₁2 ₁. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O - H⋯O hydrogen bonding there, leaving a C - H⋯O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.

Original language	English
Pages (from-to)	93-97
Number of pages	5
Journal	Journal of Chemical Crystallography
Volume	36
Issue number	2
Early online date	21 Jan 2006
DOIs	https://doi.org/10.1007/s10870-005-9004-1
Publication status	Published - Feb 2006

Keywords

Acetylation
Andrographolide
Crystal structure
Hydrogen bonding

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10.1007/s10870-005-9004-1

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title = "14-Acetylandrographolide",

abstract = "The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a- dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C 22H 32O 6, was synthesised from andrographolide. It crystallizes in the orthorhombic system with a = 7.4219(12), b = 11.8411(10), c = 23.777(4) {\AA} in space group P2 12 12 1. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O - H⋯O hydrogen bonding there, leaving a C - H⋯O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.",

keywords = "Acetylation, Andrographolide, Crystal structure, Hydrogen bonding",

author = "{Rao Jada}, Srinivasa and Katherine McMillan and Hamzah, {Ahmad S.} and Saad, {Mohammad S.} and Lajis, {Nordin H.} and Stevens, {Malcolm F G} and Schwalbe, {Carl H.} and Johnson Stanslas",

year = "2006",

month = feb,

doi = "10.1007/s10870-005-9004-1",

language = "English",

volume = "36",

pages = "93--97",

journal = "Journal of Chemical Crystallography",

issn = "1074-1542",

publisher = "Springer",

number = "2",

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TY - JOUR

T1 - 14-Acetylandrographolide

AU - Rao Jada, Srinivasa

AU - McMillan, Katherine

AU - Hamzah, Ahmad S.

AU - Saad, Mohammad S.

AU - Lajis, Nordin H.

AU - Stevens, Malcolm F G

AU - Schwalbe, Carl H.

AU - Stanslas, Johnson

PY - 2006/2

Y1 - 2006/2

N2 - The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a- dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C 22H 32O 6, was synthesised from andrographolide. It crystallizes in the orthorhombic system with a = 7.4219(12), b = 11.8411(10), c = 23.777(4) Å in space group P2 12 12 1. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O - H⋯O hydrogen bonding there, leaving a C - H⋯O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.

AB - The title compound, 3-{2-[decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a- dimethyl-2-methylene-1-napthalenyl]ethylidene}dihydro-4-acetoxy-2(3H)-furanone, C 22H 32O 6, was synthesised from andrographolide. It crystallizes in the orthorhombic system with a = 7.4219(12), b = 11.8411(10), c = 23.777(4) Å in space group P2 12 12 1. While the stereochemical relation between rings is slightly changed from the starting material, acetylation of the hydroxyfuranone moiety completely abolishes O - H⋯O hydrogen bonding there, leaving a C - H⋯O interaction. The hydrogen-bonded chains at the opposite end of the andrographolide molecule persist but reverse direction.

KW - Acetylation

KW - Andrographolide

KW - Crystal structure

KW - Hydrogen bonding

UR - http://www.scopus.com/inward/record.url?scp=33745518801&partnerID=8YFLogxK

U2 - 10.1007/s10870-005-9004-1

DO - 10.1007/s10870-005-9004-1

M3 - Article

AN - SCOPUS:33745518801

SN - 1074-1542

VL - 36

SP - 93

EP - 97

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

IS - 2

ER -

14-Acetylandrographolide

Abstract

Keywords

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