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Nucleosides and nucleotides

Tomatine

Also known as Lycopersicin, alpha-Tomatine, Tomatin

CAS 17406-45-0Formula C50H83NO21Molar mass 1,034.20 g/molEC 241-429-5
GHS signal word: Warning. Pictograms: Harmful or irritant 7 suppliers listed
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Tomatine chemical structure, C50H83NO21, CAS 17406-45-0
2D chemical structure

Key facts

What buyers check first

All properties
Appearance
Needles from methanol
Melting point
263 to 268
Solubility
SOLUBLE IN ETHANOL, METHANOL, DIOXANE, PROPYLENE GLYCOL, PRACTICALLY INSOLUBLE IN WATER,…
HS code
293979
Category
Nucleosides and nucleotides
Illustrative photo, assorted laboratory chemical bottles and jars on a laboratory bench
Typical packagingIllustrative packaging image, not the actual product

What is Tomatine?

Plain description, key identifiers and synonyms

Tomatine is a steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. It has a role as an antifungal agent, a phytotoxin and an immunological adjuvant. It is a glycoalkaloid, a glycoside, a steroid alkaloid, a tetrasaccharide derivative and an alkaloid antibiotic. It is functionally related to a tomatidine.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
CAS number
17406-45-0 CAS number cross-checked
EC number
241-429-5
Molecular formula
C50H83NO21
UNII
31U6547O08
MDL number
MFCD32005103
InChIKey
REJLGAUYTKNVJM-SGXCCWNXSA-N
InChI
InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1
Canonical SMILES
CC1CCC2(NC1)OC1CC3C4CCC5CC(OC6OC(CO)C(OC7OC(CO)C(O)C(OC8OCC(O)C(O)C8O)C7OC7OC(CO)C(O)C(O)C7O)C(O)C6O)CCC5(C)C4CCC3(C)C1C2C
Isomeric SMILES
C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1

Synonyms

  • Lycopersicin
  • alpha-Tomatine
  • Tomatin
  • A''-Tomatidine
  • Tomatidine, glycoside
  • beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-
  • (22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-[beta-D-xylopyranosyl-(1-3)]-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside
  • (22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-(beta-D-xylopyranosyl-(1-3))-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside
  • Tomatine from Tomato
  • a-tomatine
  • (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
  • Tomatine, Lycopersicin
  • (3beta,5alpha,22beta,25S)-Spirosolan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl)-(1-3))-O-(beta-D-glucopyranosyl-(1-4)-beta-D-Galactopyranoside
  • 4-27-00-01954 (Beilstein Handbook Reference)
  • (22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
  • (25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
  • (3?,5?,22?,25S)-Spirosolan-3-yl O-?-D-glucopyranosyl-(1-2)- O-[?-D-xylopyranosyl-(1-3)]-O-?-D-glucopyranosyl-(1-4)-?-D-g alactopyranoside

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Needles from methanolexp.
Melting point
263 to 268exp.
Solubility
SOLUBLE IN ETHANOL, METHANOL, DIOXANE, PROPYLENE GLYCOL, PRACTICALLY INSOLUBLE IN WATER, ETHER, PETROLEUM ETHERexp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
1,034.20 g/molcalc.
Exact mass
1,033.5458 Dacalc.
LogP (octanol/water)
-2.7calc.
Topological polar surface area
337.9 Ųcalc.
Hydrogen bond donors
13calc.
Hydrogen bond acceptors
22calc.
Rotatable bonds
11calc.
Heavy atoms
72calc.
Rings
10calc.
Aromatic rings
0calc.
Fraction sp3 carbons
1calc.
Formal charge
0calc.
Stereocentres
31calc.
Lipinski rule of five
Fails (3 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, C1CCC2(CC3C(CC4C3CCC3C5CCC(OC6CCC(OC7OCCC(OC8CCCCO8)C7OC7CCCCO7)CO6)CC5CCC34)O2)NC1

C1CCC2(CC3C(CC4C3CCC3C5CCC(OC6CCC(OC7OCCC(OC8CCCCO8)C7OC7CCCCO7)CO6)CC5CCC34)O2)NC1

10 rings, 53 atoms.

3 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Warning
GHS07: Harmful or irritant
Harmful or irritant

Hazard statements

  • H302Harmful if swallowed.
Precautionary statements (5)
  • P264Wash skin thoroughly after handling.
  • P270Do not eat, drink or smoke when using this product.
  • P301 + P317If swallowed: Get medical help.
  • P330Rinse mouth.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Tomatine suppliers

Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings

All 7 suppliers
7 of 7 offers

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Where suppliers are based

7 suppliers in 2 countries

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Tomatine price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Precipitating agent for steroids, proposed as an alternate precipitant to digitonin.

Used as plant fungicide and as a specific precipitating agent for cholesterol.

Pharmacological actions

  • Anti-Infective Agents
  • Antifungal Agents
  • Indicators and Reagents

Roles

  • adjuvant
  • antifungal agent
  • antimicrobial agent
  • eukaryotic metabolite
  • immunological adjuvant
  • immunomodulator
  • metabolite
  • pharmaceutical
  • phytotoxin
  • plant metabolite
  • poison
  • toxin

How it is made

A glycosidal alkaloid prepared from the dried leaves and stems of the tomato plant. ... The crude extract is referred to as tomatin.

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Tomatine is traded under.

HS 2939.79Indicative HS code

Alkaloids of vegetal origin, other than cocaine, ecgonine, salts, esters and other derivatives, not elsewhere…

World exports in 2024
$701M
+18.9% vs 2023, imports $830M
2019 to 2024
Top exporters
  1. Switzerland * partner reported25.3%
  2. Germany21.4%
  3. India * partner reported14.9%
Top importers
  1. United States20.9%
  2. Germany14.7%
  3. Italy14.6%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Tomatine is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Tomatine, based on the data on this page

What is Tomatine?

Tomatine is a steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose. It has a role as an antifungal agent, a phytotoxin and an immunological adjuvant.

What is the CAS number of Tomatine?

The CAS registry number of Tomatine is 17406-45-0.

What is the molecular formula and weight of Tomatine?

The molecular formula of Tomatine is C50H83NO21 and its molar mass is 1,034.20 g/mol.

What is Tomatine used for?

Precipitating agent for steroids, proposed as an alternate precipitant to digitonin. Used as plant fungicide and as a specific precipitating agent for cholesterol.

Is Tomatine hazardous?

Tomatine carries the GHS signal word "Warning". Main hazards: harmful if swallowed. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Tomatine?

Tomatine is usually classified under HS code 293979 (Alkaloids, natural or reproduced by synthesis, and their salts, ethers, esters and other…). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Tomatine?

CompoundList lists 7 suppliers of Tomatine in United States and China. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Tomatine?

Suppliers quote Tomatine on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Tomatine

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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