28789-35-7

Basic information

• Product Name: NORDIHYDROCAPSAICIN
• Synonyms: NORDIHYDROCAPSAICIN;N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyl-octanamide;Norhydrocapsaicin;N-(4-Hydroxy-3-methoxybenzyl)-7-methyloctanamide
• CAS NO: 28789-35-7
• Molecular Formula: C₁₇H₂₇NO₃
• Molecular Weight: 293.4
• Product Categories: Miscellaneous Natural Products
• Mol File: 28789-35-7.mol

Chemical Properties

• Boiling Point: 487 °C at 760 mmHg
• Flash Point: 248.3 °C
• Appearance: /
• Density: 1.036±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 4.15E-10mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: 2-8°C
• PKA: 9.76±0.20(Predicted)
• CAS DataBase Reference: NORDIHYDROCAPSAICIN(CAS DataBase Reference)
• NIST Chemistry Reference: NORDIHYDROCAPSAICIN(28789-35-7)
• EPA Substance Registry System: NORDIHYDROCAPSAICIN(28789-35-7)

Safety Data

• Hazardous Substances Data: 28789-35-7(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
NORDIHYDROCAPSAICIN is used as a flavor enhancer for its spicy taste, adding a unique heat to various food products.
Used in Pain Management:
NORDIHYDROCAPSAICIN is used as an analgesic agent for its potential pain-relieving properties, particularly in conditions like arthritis and neuropathy.
Used in Protective or Deterrent Products:
NORDIHYDROCAPSAICIN is used as an active ingredient in pepper sprays for its irritant effects, providing protection and deterrence against potential threats.

InChI:InChI=1/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)

Synthetic route

Vanillylamin (1196-92-5) + 7-methyloctanoyl chloride (122876-14-6) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
In diethyl ether 1.) room temp., overnight, 2.) reflux, 3 h; Yield given;

(Z)-N-(4-hydroxy-3-methoxybenzyl)-7-methyloct-5-enamide (112375-60-7) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;

norcapsaicin (61229-08-1) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;

isononoic acid (693-19-6) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) SOCl2 / 1.) room temp., 3 h, 2.) reflux, 2 h 2: diethyl ether / 1.) room temp., overnight, 2.) reflux, 3 h View Scheme

7-methyl-6-oxooctanoic acid (59210-01-4) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / KOH, N2H4*H2O / bis-(2-hydroxy-ethyl) ether / 23 h / Heating 2: 1.) SOCl2 / 1.) room temp., 3 h, 2.) reflux, 2 h 3: diethyl ether / 1.) room temp., overnight, 2.) reflux, 3 h View Scheme

Vanillylamin (1196-92-5) + piperinic acid chloride → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 72 h / Ambient temperature 2: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / 72 h / Ambient temperature 2: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

methyl 4-formylbutanoate (6026-86-4) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h 2: aq. KOH / ethanol / 1 h / Heating 3: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 4: diethyl ether / 72 h / Ambient temperature 5: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme
Multi-step reaction with 6 steps 2: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 3: aq. KOH / ethanol / 1 h / Heating 4: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 5: diethyl ether / 72 h / Ambient temperature 6: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

methyl 5-hydroxypentanoate (14273-92-8) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature 2: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h 3: aq. KOH / ethanol / 1 h / Heating 4: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 5: diethyl ether / 72 h / Ambient temperature 6: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme
Multi-step reaction with 7 steps 1: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature 3: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 4: aq. KOH / ethanol / 1 h / Heating 5: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 6: diethyl ether / 72 h / Ambient temperature 7: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

(E)-7-Methyloct-5-enoic acid (61229-06-9) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 2: diethyl ether / 72 h / Ambient temperature 3: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

(Z)-7-Methyl-oct-5-enoic acid (81077-23-8) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 2: diethyl ether / 72 h / Ambient temperature 3: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

Benzoic acid 2-benzenesulfonyl-1-(3-methoxycarbonyl-propyl)-3-methyl-butyl ester → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 2: aq. KOH / ethanol / 1 h / Heating 3: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 4: diethyl ether / 72 h / Ambient temperature 5: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

(Z)-7-Methyl-oct-5-enoyl chloride (112375-57-2) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 72 h / Ambient temperature 2: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

(E)-7-Methyloct-5-enoic acid chloride (112375-57-2) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 72 h / Ambient temperature 2: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

(Z)-methyl 7-methyloct-5-enoate (112375-41-4) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH / ethanol / 1 h / Heating 2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 3: diethyl ether / 72 h / Ambient temperature 4: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

(E)-methyl 7-methyloct-5-enoate (112375-53-8) → Nordihydrocapsaicin (28789-35-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH / ethanol / 1 h / Heating 2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 3: diethyl ether / 72 h / Ambient temperature 4: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

Nordihydrocapsaicin (28789-35-7) + salicylic acid (69-72-7) → 7-methyl-N-(4-salicyloyloxy-3-methoxyphenylmethyl)octamide

Conditions	Yield
Stage #1: salicylic acid With thionyl chloride; triethylamine at 80℃; for 1h; Stage #2: Nordihydrocapsaicin With triethylamine In acetone at 10℃; for 5.5h; Cooling with ice;

Upstream product

• 1196-92-5 Vanillylamin 
• 122876-14-6 7-methyloctanoyl chloride 
• 112375-60-7 (Z)-N-(4-hydroxy-3-methoxybenzyl)-7-methyloct-5-enamide 
• 61229-08-1 norcapsaicin 
• 693-19-6 isononoic acid 
• 59210-01-4 7-methyl-6-oxooctanoic acid 
• 6026-86-4 methyl 4-formylbutanoate 
• 14273-92-8 methyl 5-hydroxypentanoate 
• 61229-06-9 (E)-7-Methyloct-5-enoic acid 
• 81077-23-8 (Z)-7-Methyl-oct-5-enoic acid 
• 112375-57-2 (Z)-7-Methyl-oct-5-enoyl chloride 
• 112375-57-2 (E)-7-Methyloct-5-enoic acid chloride 
• 112375-41-4 (Z)-methyl 7-methyloct-5-enoate 
• 112375-53-8 (E)-methyl 7-methyloct-5-enoate 

Relevant articles and documents

Method for industrial purification of capsaicin

The invention provides a method for industrial purification of Capsaicin in high purity from capsinoids (Capsaicin and analogues), more specifically, a method for industrial purification of Capsaicin which comprises contacting capsinoids containing Capsaicin in a hydrophilic solvent with a silver compound in an aqueous solution to form a Capsaicin-silver complex which is soluble in water, and recovering highly pure Capsaicin from the Capsaicin-silver complex without chromatography.

A Short Route to Dihydrocapsaicinoids

Huang-Minlon reduction of 8-methyl-7-oxononanoic acid (4ba), obtained by the acylation of cyclohexanone enamine 2a with 2-methylpropanoyl chloride (1b) followed by ring cleavage of the resultant β-diketone 3ba affords 8-methylnonanoic acid (5ba), the chloride of which reacts readily with 4-hydroxy-3-methoxybenzylamine to give dihydrocapsaicin (7ba).This reaction sequence works also efficiently for other dihydrocapsaicinoids such as 7aa and 7bb.

The Capsaicinoids: Their Separation, Synthesis, and Mutagenicity

Capsaicin (1b), the pungent ingredient in many varietes of Capsicums has recently been implicated as a possible carcinogen.When obtained from natural sources 1b is always accompanied by a number of related homologues.We have isolated seven of these homologues, characterized them, and synthesized them by a general and unique route developed in our laboratories.Also reported are mutagenicity data for 1b and an extract of red pepper as measured by the Ames assay and the V-79 mammalian cell assay.