We Offer Worldwide Shipping
Login Wishlist

(S)-(-)-α-Terpineol

$52

  • Brand : BIOFRON

  • Catalogue Number : BD-D1255

  • Specification : 98%(HPLC)

  • CAS number : 10482-56-1

  • Formula : C10H18O

  • Molecular Weight : 154.25

  • PUBCHEM ID : 443162

  • Volume : 0.5ML

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

BD-D1255

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

154.25

Appearance

Colorless liquid

Botanical Source

Pinus tabulac formis Carr; Pinus massoniana Lamb.

Structure Type

Monoterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CCC(CC1)C(C)(C)O

Synonyms

p-Menth-1-en-8-ol, (S)-(-)-/(S)-(-)-alpha-terpineol/L-α-TERPINEOL/(S)-p-Menth-1-en-8-ol/2-[(1S)-4-Methyl-3-cyclohexen-1-yl]-2-propanol/(-)-a-Terpineol/(S)-a-Terpineol/(S)-(-)-α-Terpineol/3-Cyclohexene-1-methanol, α,α,4-trimethyl-, (S)-/2-[(1S)-4-Methylcyclohex-3-en-1-yl]propan-2-ol/l-a-Terpineol/α-Terpineol/3-Cyclohexene-1-methanol, α,α,4-trimethyl-, (1S)-/(S)-2-(4-Methyl-3-cyclohexenyl)-2-propanol

IUPAC Name

2-[(1S)-4-methylcyclohex-3-en-1-yl]propan-2-ol

Applications

Density

0.9±0.1 g/cm3

Solubility

Flash Point

89.4±0.0 °C

Boiling Point

217.5±0.0 °C at 760 mmHg

Melting Point

31-35ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2906190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:10482-56-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27729471

Abstract

Flowers of Nicotiana species emit a characteristic blend including the cineole cassette monoterpenes. This set of terpenes is synthesized by multiproduct enzymes, with either 1,8-cineole or α-terpineol contributing most to the volatile spectrum, thus referring to cineole or terpineol synthase, respectively. To understand the molecular and structural requirements of the enzymes that favor the biochemical formation of α-terpineol and 1,8-cineole, site-directed mutagenesis, in silico modeling, and semiempiric calculations were performed. Our results indicate the formation of α-terpineol by a nucleophilic attack of water. During this attack, the α-terpinyl cation is stabilized by π-stacking with a tryptophan side chain (tryptophan-253). The hypothesized catalytic mechanism of α-terpineol-to-1,8-cineole conversion is initiated by a catalytic dyad (histidine-502 and glutamate-249), acting as a base, and a threonine (threonine-278) providing the subsequent rearrangement from terpineol to cineol by catalyzing the autoprotonation of (S)-(-)-α-terpineol, which is the favored enantiomer product of the recombinant enzymes. Furthermore, by site-directed mutagenesis, we were able to identify amino acids at positions 147, 148, and 266 that determine the different terpineol-cineole ratios in Nicotiana suaveolens cineole synthase and Nicotiana langsdorffii terpineol synthase. Since amino acid 266 is more than 10 a away from the active site, an indirect effect of this amino acid exchange on the catalysis is discussed.
© 2016 American Society of Plant Biologists. All Rights Reserved.

Title

The α-Terpineol to 1,8-Cineole Cyclization Reaction of Tobacco Terpene Synthases

Author

Birgit Piechulla 1 2 3 , Richard Bartelt 4 5 6 , Anne Brosemann 4 5 6 , Uta Effmert 4 5 6 , Harro Bouwmeester 4 5 6 , Frank Hippauf 4 5 6 , Wolfgang Brandt 4 5 6

Publish date

2016 Dec

PMID

30540974

Abstract

Diarrhea is one of the leading causes of infant death in the world accounting for high child mortality rate. It is also present in different pathophysiologies related to several etiological agents. The aim of this study is to investigate the antidiarrheal effect of α -Terpineol (α-TPN) in different diarrhea models in rodents. The antidiarrheal effect of α-TPN in the treatment of acute diarrhea and enteropooling induced by castor oil or PGE2 in Swiss mice pretreated orally with saline (NaCl 0.9%), Loperamide (5 mg/kg) and α-TPN (6.25, 12.5, 25 and 50 mg/kg) was analyzed. Additionally, parameters of severity, total weight of faeces and post-treatment for 4 h were evaluated. Modulation of the opioid and cholinergic pathways was performed and intestinal transit model using activated charcoal as marker was also used. The effect of α-TPN on secretory diarrhea was investigated using the model of fluid secretion in intestinal loops isolated from cholera toxin-treated mice. α-TPN showed antidiarrheal effect (*p < 0.05), reducing the total stool amount (*55%, *48%, *44%, *24%) and diarrheal (*47%, *66%; *56%, 10%) respectively for the doses tested. All doses investigated in the enteropooling test presented significant changes (*46%, *78%, *66%, *41% respectively) in relation to the control. α-TPN through the muscarinic pathway reduced the gastrointestinal transit (*31%), besides inhibiting PGE2-induced diarrhea (*39%). α-TPN also reduced fluid formation and loss of Cl- ions, by interacting directly with GM1 receptors and cholera toxin, thus increasing the uptake of intestinal fluids. The results suggest an anti-diarrheal activity of α-TPN due to its anticholinergic action, ability to block PGE2 and GM1 receptors and interaction with cholera toxin in secretory diarrhea, making it a promising candidate drug for the treatment of diarrheal diseases.

KEYWORDS

Castor oil; Cholera; Diarrhea; GM1 receptor; Monoterpenes; Prostaglandin E(2).

Title

Antidiarrheal Activity of α-Terpineol in Mice

Author

Polyanna Dos Santos Negreiros 1 , Douglas Soares da Costa 1 , Valdelania Gomes da Silva 1 , Izabela Borges de Carvalho Lima 1 , Daniel Barbosa Nunes 1 , Francisca Beatriz de Melo Sousa 2 , Thiago de Souza Lopes Araújo 2 , Jand Venes Rolim Medeiros 2 , Rosimeire Ferreira Dos Santos 1 , Rita de Cassia Meneses Oliveira 3

Publish date

2019 Feb

PMID

27124242

Abstract

α-Terpineol is a monoterpene with smooth muscle relaxant properties. In this study, its effects on the gastric emptying rate of awake rats were evaluated with emphasis on the mode by which it induces gastrointestinal actions. Administered by gavage, α-terpineol (50 mg/kg) delayed gastric emptying of a liquid test meal at 10 min postprandial. Hexamethonium or guanethidine did not interfere with the retarding effect induced by α-terpineol, but atropine and L-NG-nitroarginine methyl ester abolished it. In vagotomized rats, α-terpineol did not delay gastric emptying. In isolated strips of gastric fundus, concentration-effect curves in response to carbamylcholine were higher in magnitude after treatment with the monoterpene. α-Terpineol (1 to 2000 µM) relaxed sustained contractions induced by carbamylcholine or a high K+ concentration in a concentration-dependent manner. This relaxing effect was not affected by the presence of L-NG-nitroarginine methyl ester, 1 H-[1, 2, 4]oxadiazolo[4,3-a]quinoxalin-1-one, tetraethylammonium, or atropine. Smooth muscle contractions induced by electrical field stimulation were inhibited by α-terpineol. In conclusion, α-terpineol induced gastric retention in awake rats through mechanisms that depended on intact vagal innervation to the stomach, which involved cholinergic/nitrergic signalling. Such a retarding effect induced by α-terpineol appears not to result from a direct action of the monoterpene on gastric smooth muscle cells.
Georg Thieme Verlag KG Stuttgart · New York.

Title

α-Terpineol Induces Gastric Retention of Liquids by Inhibiting Vagal Parasympathetic Pathways in Rats

Author

Moises Tolentino Bento da Silva 1 , Rosemarie Brandim Marques 2 , Francisco Jose Batista-Lima 3 , Marilia Almeida Soares 3 , Armênio Aguiar Dos Santos 3 , Pedro Jorge Caldas Magalhães 3 , Francisco de Assis Oliveira 2 , Fernanda Regina de Castro Almeida 2

Publish date

2016 Oct