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S8754

Sigma-Aldrich

Solanesol from tobacco

≥90% (HPLC)

Synonym(s):

Betulanonaprenol, Nonaisoprenol

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About This Item

Empirical Formula (Hill Notation):
C45H74O
CAS Number:
13190-97-1
Molecular Weight:
631.07
MDL number:
MFCD00070279
UNSPSC Code:
12352212
PubChem Substance ID:
24899813
NACRES:
NA.25

Assay

≥90% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

C\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO

InChI

1S/C45H74O/c1-37(2)19-11-20-38(3)21-12-22-39(4)23-13-24-40(5)25-14-26-41(6)27-15-28-42(7)29-16-30-43(8)31-17-32-44(9)33-18-34-45(10)35-36-46/h19,21,23,25,27,29,31,33,35,46H,11-18,20,22,24,26,28,30,32,34,36H2,1-10H3/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-33+,45-35+

InChI key

AFPLNGZPBSKHHQ-MEGGAXOGSA-N

Related Categories

General description

Solanesol is mainly extracted from Nicotiana tabacum (tobacco). It is an aliphatic terpene, polyisoprenoid alcohol. Solanesol can also be found in other solanaceous plants such as tomato (Solanum lycopersicum), potato (Solanum tuberosum), eggplant, bell peppers.This C45 isoprenoid alcohol is the most abundant lipid in tobacco leaves.

Application

Solanesol from tobacco has been used as a reference standard for the quantification of solanesol from different tobacco leaf samples using reverse-phase high-performance liquid chromatography (RP-HPLC). It has also been used to increase the stability of artificial liposomes to test the mechanical function of ubiquinone-8 (Q8)-mediated membrane stabilization in E. coli under osmotic stress.

Biochem/physiol Actions

Solanesol displays antioxidant, anti-inflammatory, neuroprotective, and antimicrobial activities. It also exerts anti-cancer properties as a therapeutic carrier by binding together with thiosalicyclic acid (TS) and hyaluronic acid (HA).Solanesol may be an important precursor of the tumorigenic polynuclear aromatic hydrocarbons of smoke.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jiangyong Hu et al.
Se pu = Chinese journal of chromatography, 25(4), 528-531 (2007-11-01)
Preparative high-speed counter-current chromatography (HSCCC) was used for the isolation and purification of solanesol from potato leaves. Experimental conditions of the extraction of solanesol from potato leaves have been optimized. An ultrafine extraction method was applied in this study. The
Jian-Hong Wang et al.
Journal of Asian natural products research, 11(11), 978-984 (2010-02-26)
Novel solanesylpiperazinotriamines as well as their N-aryl-substituted analogs were synthesized starting from solanesol through a multistep procedure. Their structures were confirmed by IR, (1)H NMR, MS, and elemental analysis. The preliminary results indicated that these novel derivatives were preferentially toxic
Severson, R.F., et al.
Journal of Chromatographic Science, 139, 269-269 (1977)
R Nageswara Rao et al.
Journal of pharmaceutical and biomedical analysis, 46(2), 310-315 (2007-11-27)
A method of continuous counter current extraction in a large-scale production of solanesol from tobacco leaves was developed. The crude extract containing 15-20% solanesol was subjected to a series of steps, viz., saponification, solvent recrystallization and column chromatography. The pure
Peter A Machado et al.
Bioresource technology, 101(3), 1091-1096 (2009-09-24)
Solanesol in the waste streams of a bioprocess designed for alternative applications of low-alkaloid tobacco was recovered using three different extraction methods. Compared to the conventional heat-reflux extraction (HRE) and ultrasound-assisted extraction (UAE), microwave-assisted extraction (MAE) using 1:3 hexane:ethanol (v/v)
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