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Merck
CN

S8754

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
NACRES:
NA.25
PubChem Substance ID:
24899813
UNSPSC Code:
12352212
MDL number:
MFCD00070279

Key Documents

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Product Name

Solanesol from tobacco, ≥90% (HPLC)

InChI key

AFPLNGZPBSKHHQ-MEGGAXOGSA-N

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+

assay

≥90% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

Quality Level

200

Related Categories

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000382340
0000382342
0000382342
0000382340
128H5859

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Mark A Taylor et al.
Phytochemistry, 72(11-12), 1323-1327 (2011-04-05)
Isoprenoids, also known as terpenoids, are the largest and oldest class of natural products known. They are comprised of more than 40,000 different molecules all biosynthetically related via a common five carbon building block (isopentenyl). Many isoprenoids are of commercial
Junhui Chen et al.
Journal of separation science, 31(1), 137-142 (2007-12-21)
HPLC coupled online with atmospheric pressure chemical ionization MS (APCI-MS) technique was evaluated for the qualitative and quantitative determination of solanesol in extracts of tobacco leaves. The solanesol and other compounds in the extract were separated on an Alltima C(8)
Yao Xiong et al.
International journal of pharmaceutics, 572, 118823-118823 (2019-11-13)
Metabolites of a large number of inert drug carriers can cause long-term exogenous biological toxicity. Therefore, carriers with simultaneous therapeutic effects may be a good choice for drug delivery. Herein, a series of pharmacologically active solanesol derivatives were synthesized and
Daniel C Sévin et al.
Nature chemical biology, 10(4), 266-272 (2014-02-11)
Bacteria are thought to cope with fluctuating environmental solute concentrations primarily by adjusting the osmolality of their cytoplasm. To obtain insights into the underlying metabolic adaptations, we analyzed the global metabolic response of Escherichia coli to sustained hyperosmotic stress using
Weihong Zhong et al.
Applied microbiology and biotechnology, 89(2), 293-302 (2010-09-22)
In a water-organic solvent, two-phase conversion system, CoQ(10) could be produced directly from solanesol and para-hydroxybenzoic acid (PHB) by free cells of Sphingomonas sp. ZUTE03 and CoQ(10) concentration in the organic solvent phase was significantly higher than that in the
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