Absinthin (Standard)

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Description

Absinthin (Standard) is the analytical standard of Absinthin. This product is intended for research and analytical applications. Absinthin is a structurally unique triterpene, and is responsible for the high bitter value of wormwood. Absinthin is an agonist of the bitter taste receptor hTAS2R46, which reduces cytosolic Ca2+-rises induced by histamine by a receptor-specific mechanism mediated by hTAS2R46[1][2][3].

CAS Number

1362-42-1

UNSPSC

12352005

Target

Others; Reference Standards

Type

Reference compound

Related Pathways

Others

Field of Research

Others

Assay Protocol

https://www.medchemexpress.com/absinthin-standard.html

Smiles

CC1=C[C@@]2([H])[C@]3([H])[C@]1([C@](OC4=O)([H])[C@@]([C@@H]4C)([H])CC[C@@]3(O)C)[C@]5([H])[C@@]2([H])[C@]([C@]6(O)C)([H])C([C@](OC7=O)([H])[C@@]([C@@H]7C)([H])CC6)=C5C

Molecular Formula

C30H40O6

Molecular Weight

496.64

References & Citations

[1]Zhang W, et al. Total synthesis of absinthin. J Am Chem Soc. 2005 Jan 12;127 (1) :18-9.|[2]Lachenmeier DW, et al. Absinthe--a review. Crit Rev Food Sci Nutr. 2006;46 (5) :365-77.|[3]Talmon M, et al. Absinthin, an agonist of the bitter taste receptor hTAS2R46, uncovers an ER-to-mitochondria Ca2+-shuttling event. J Biol Chem. 2019 Aug 16;294 (33) :12472-12482.|[4]Guo N, et al. Absinthin attenuates LPS-induced ALI through MIP-1α-mediated inflammatory cell infiltration. Exp Lung Res. 2015;41 (9) :514-24. |[5]Talmon M, et al. Anti-inflammatory Activity of Absinthin and Derivatives in Human Bronchoepithelial Cells. J Nat Prod. 2020 Jun 26;83 (6) :1740-1750.|[6]Zhang W, et al. Total synthesis of absinthin. J Am Chem Soc. 2005 Jan 12;127 (1) :18-9.|[7]Lachenmeier DW, et al. Absinthe--a review. Crit Rev Food Sci Nutr. 2006;46 (5) :365-77.|[8]Talmon M, et al. Absinthin, an agonist of the bitter taste receptor hTAS2R46, uncovers an ER-to-mitochondria Ca2+-shuttling event. J Biol Chem. 2019 Aug 16;294 (33) :12472-12482.|[9]Guo N, et al. Absinthin attenuates LPS-induced ALI through MIP-1α-mediated inflammatory cell infiltration. Exp Lung Res. 2015;41 (9) :514-24. |[10]Talmon M, et al. Anti-inflammatory Activity of Absinthin and Derivatives in Human Bronchoepithelial Cells. J Nat Prod. 2020 Jun 26;83 (6) :1740-1750.

Shipping Conditions

Room temperature

Scientific Category

Reference Standards

Chemical Information

Absinthin

Absinthin is a dimeric sesquiterpene lactone that is produced by the plant Artemisia absinthium (Wormwood). The bitter tasting constituent of Absinthe. It has a role as an anti-inflammatory agent and a plant metabolite. It is a triterpenoid, a sesquiterpene lactone and an organic heteroheptacyclic compound.

CAS Number	1362-42-1
PubChem CID	442138
IUPAC Name	(1R,2R,5S,8S,9S,12S,13R,14S,15S,16R,17S,20S,21S,24S)-12,17-dihydroxy-3,8,12,17,21,25-hexamethyl-6,23-dioxaheptacyclo[13.9.2.01,16.02,14.04,13.05,9.020,24]hexacosa-3,25-diene-7,22-dione
Molecular Formula	C30H40O6
Molecular Weight	496.6
XLogP	2.2
Topological Polar Surface Area	93.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	0
Heavy Atom Count	36
Formal Charge	0
Complexity	1140

SMILES

C[C@H]1[C@@H]2CC[C@]([C@@H]3[C@H]4[C@H]5C=C([C@@]6([C@H]4C(=C3[C@H]2OC1=O)C)[C@@H]5[C@@](CC[C@@H]7[C@@H]6OC(=O)[C@H]7C)(C)O)C)(C)O

InChI

InChI=1S/C30H40O6/c1-12-11-18-20-21(30(12)24(18)29(6,34)10-8-17-14(3)27(32)36-25(17)30)15(4)19-22(20)28(5,33)9-7-16-13(2)26(31)35-23(16)19/h11,13-14,16-18,20-25,33-34H,7-10H2,1-6H3/t13-,14-,16-,17-,18+,20-,21-,22-,23-,24-,25-,28-,29-,30+/m0/s1

InChIKey

PZHWYURJZAPXAN-ILOFNVQHSA-N

Chemical Structure

2D Structure

CAS: 1362-42-1

CID: 442138

Formula: C30H40O6

MW: 496.6

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	496.6
XLogP3	2.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	0
Exact Mass	496.28248899
Monoisotopic Mass	496.28248899
Topological Polar Surface Area	93.1 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	1140
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Absinthin (Standard)

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