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Ingenol

Ingenol Structure
Ingenol structure
CAS No.
30220-46-3
Chemical Name:
Ingenol
Synonyms
Ingeno;INGENOL;Inglenook;Ingenol, BR;(-)-Ingenol;Ingenol >99%;Ingenol base;Ingenol USP/EP/BP;INGENOL,HIGHPURITY;Ingenol 30220-46-3
CBNumber:
CB4370581
Molecular Formula:
C20H28O5
Molecular Weight:
348.43
MDL Number:
MFCD27980538
MOL File:
30220-46-3.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-14 16:49:18
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Ingenol Properties

Melting point 153 °C
Boiling point 523.8±50.0 °C(Predicted)
Density 1.33±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility DMSO: soluble
form film
pka 12.06±0.70(Predicted)
color colorless
InChIKey VEBVPUXQAPLADL-POYOOMFHSA-N
SMILES [C@@]12(O)[C@@H](O)C(C)=C[C@@]31C(=O)[C@@]([H])(C=C(CO)[C@H]2O)[C@]1([H])C(C)(C)[C@]1([H])C[C@H]3C
FDA UNII IC77UZI9G8

SAFETY

Risk and Safety Statements

Symbol(GHS)  Corrosion (GHS05)
GHS05
Signal word  Danger
Hazard statements  H315-H318
Precautionary statements  P280-P305+P351+P338
Hazard Codes  Xi
Risk Statements  38-41
Safety Statements  26-36
WGK Germany  3
HS Code  2914409000

Ingenol price More Price(77)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical I1112 Ingenol 30220-46-3 10MG $88 2026-04-30 Buy
TCI Chemical I1112 Ingenol 30220-46-3 50MG $281 2026-04-30 Buy
Cayman Chemical 14031 Ingenol ≥98% 30220-46-3 500μg $38 2026-04-30 Buy
Cayman Chemical 14031 Ingenol ≥98% 30220-46-3 1mg $65 2026-04-30 Buy
Cayman Chemical 14031 Ingenol ≥98% 30220-46-3 5mg $274 2026-04-30 Buy
Product number Packaging Price Buy
I1112 10MG $88 Buy
I1112 50MG $281 Buy
14031 500μg $38 Buy
14031 1mg $65 Buy
14031 5mg $274 Buy

Ingenol Chemical Properties, Uses, Production

Description

Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus.1 It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.

Chemical Properties

Isolated in 1968, ingenol, a highly oxygenated tetracyclic diterpene classified as a member of the phorboid family, is the parent compound of several dozen naturally occurring ingenanes that possess the same carbon skeleton but varied peripheral functionalities. In addition to their intriguing “inside-outside” bridged BC ring system, the ingenanes display interesting biological profiles that range from tumorpromoting to anti-leukemic and anti-HIV activities. Since the early 1980s, this combination of important biological function and complex architecture has inspired the efforts of numerous synthetic chemists.4 Previously, we reported an approach toward 1 wherein known â-ketoester 2 was advanced to diene 3, which served as a ring-closing metathesis substrate in a first generation Grubbs reaction that delivers the ingenane tetracycle 4.
Grubbs reaction

Ingenol mebutate

Ingenol mebutate is a selective small-molecule activator of protein kinase C (PKC) isolated from the plant Euphorbia peplus with potential antineoplastic activity. Ingenol mebutate activates various protein kinase C (PKC) isoforms, thereby inducing apoptosis in some tumor cells, including myeloid leukemia cells, melanoma cells, and basal cell carcinoma cells. The PKC family consists of signaling isoenzymes that regulate many cell processes including proliferation, differentiation, and apoptosis.
Ingenol mebutate was approved by the FDA in January 2012, and it is marketed under the name Picato®. Picato gel is indicated for the topical treatment of actinic keratosis. Before approval, ingenol mebutate was called PEP005 as an investigational drug. PEP005 is a selective small molecule activator of protein kinase C (PKC) extracted from the plant Euphorbia peplus, whose sap has been used as a traditional medicine for the treatment of skin conditions including warts and cancer. PEP005 also has potent anti-leukemic effects, inducing apoptosis in myeloid leukemia cell lines and primary AML cells at nanomolar concentrations.
Ingenol mebutate gel (Picato) is a topical cream that the manufacturer is requesting to use as a secondline treatment in patients with actinic keratosis (AK) who have failed or are intolerant to 5-fluorouracil (5-FU). Ingenol mebutate gel is available in two strengths – a 0.015% dose for lesions on the face and scalp and a 0.05% dose for lesions on the trunk and extremities.

Pharmacokinetics & metabolism

The pharmacokinetics investigation of the systemic absorption of ingenol mebutate gel 0.05% was evaluated in a randomized vehicle-controlled double blind study, in which 1 g was applied to a contiguous 100 cm2 area of multiple AKs on the dorsal forearms of 16 patients in two consecutive daily applications. This clinical trial showed that there was no detectable systemic absorption of the parent drug or its two principal metabolites (both acyl isomers of ingenol mebutate), when the limit of detection was 0.1 ng/ml.
In vitro studies using [3H]-ingenol mebutate showed that metabolism of the drug by human hepatocytes is extensive. Other in vitro studies showed that ingenol mebutate neither induces human CYPP450 enzymes CYP1A2, 2C9 and 3A4a, nor inhibits CYP1A2, 2A6, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1 and 3A4.

Description

Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus. It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.

Uses

Ingenol, is the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.

Definition

ChEBI: A tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by met yl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastere mer).

IC 50

PKC: 30 μM (Ki)

References

[1] P A WENDER. Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogs.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1986, 83 12: 4214-4218. DOI: 10.1073/pnas.83.12.4214
[2] C M HASLER  P M B  G Acs. Specific binding to protein kinase C by ingenol and its induction of biological responses.[J]. Cancer research, 1992, 52 1: 202-208.
[3] GERD VOGG . Tumor promoting diterpenes from Euphorbia leuconeura L.[J]. Phytochemistry, 1999, 51 2: Pages 289-295. DOI: 10.1016/s0031-9422(99)00016-3
[4] T.J. NELSON  D. L A. Neuroprotective versus tumorigenic protein kinase C activators[J]. Trends in Biochemical Sciences, 2009, 34 3: Pages 136-145. DOI: 10.1016/j.tibs.2008.11.006
[5] MARK LEBWOHL. Ingenol mebutate gel for actinic keratosis.[J]. The New England Journal of Medicine, 2012: 1010-1019. DOI: 10.1056/nejmoa1111170

Ingenol synthesis

54706-99-9
30220-46-3
Synthesis of Ingenol from 20-DEOXYINGENOL

Ingenol Preparation Products And Raw materials

Raw materials

1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 4-[(acetyloxy)methyl]-1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)- 20-DEOXYINGENOL Ingenol mebutate

Preparation Products

(1aR)-5β,6β-Bis(benzoyloxy)-1aα,2,5,5a,6,9,10,10aα-octahydro-5aβ-hydroxy-4-(hydroxymethyl)-1,1,7,9α-tetramethyl-1H-2α,8aα-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one

Ingenol Suppliers

Global Suppliers ( 274)
Supplier Tel Email Country ProdList Advantage
Nanjing Spring & Autumn Biological Engineering Co., Ltd. 17388075642 13815430202 sale02@cqherb.com China 261 59
Sichuan Wei Keqi Biological Technology Co., Ltd. 028-81700200 18116577057 3003855609@qq.com China 7717 56
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Chembest Research Laboratories Limited 021-20908456 sales@BioChemBest.com China 5996 61
Adamas Reagent, Ltd. 400-6009262 15618770481 yhx@titansci.com China 14098 59
Chemsky (shanghai) International Co.,Ltd 021-50135380 shchemsky@sina.com China 15350 60
Hunan Hui Bai Shi Biotechnology Co., Ltd. 0731-85526065 13308475853 ivy@hnhbsj.com China 7236 62
Dalian Meilun Biotech Co., Ltd. 0411-62910999 13889544652 sales@meilune.com China 4765 58
ShangHai YuanYe Biotechnology Co., Ltd. 15026964105 shyysw007@163.com China 4998 60
Chengdu Biopurify Phytochemicals Ltd. +86-028-82633397 18982077548 cwb1@biopurify.cn China 2376 60
Supplier Advantage
Nanjing Spring & Autumn Biological Engineering Co., Ltd. 59
Sichuan Wei Keqi Biological Technology Co., Ltd. 56
J & K SCIENTIFIC LTD. 76
Chembest Research Laboratories Limited 61
Adamas Reagent, Ltd. 59
Chemsky (shanghai) International Co.,Ltd 60
Hunan Hui Bai Shi Biotechnology Co., Ltd. 62
Dalian Meilun Biotech Co., Ltd. 58
ShangHai YuanYe Biotechnology Co., Ltd. 60
Chengdu Biopurify Phytochemicals Ltd. 60

Related articles

  • Total Synthesis of Ingenol
  • Isolated in 1968, ingenol (1), a highly oxygenated tetracyclic diterpene classified as a member of the phorboid family, is the....
  • Oct 30,2019

View Latest Price from Ingenol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ingenol pictures 2026-08-12 Ingenol
30220-46-3
 $1788.00 1KG 99% 100kg Baoji Guokang Healthchem Co., Ltd.
Ingenol pictures 2026-07-13 Ingenol
30220-46-3
 $44.00-129.00 99.87% 10g TargetMol Chemicals Inc.
Ingenol pictures 2023-04-04 Ingenol
30220-46-3
 $400.00 1KG 99% 10kg Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd.
  • Ingenol pictures
  • Ingenol
    30220-46-3
  • $1788.00
  • 99%
  • Baoji Guokang Healthchem Co., Ltd.
  • Ingenol pictures
  • Ingenol
    30220-46-3
  • $44.00-129.00
  • 99.87%
  • TargetMol Chemicals Inc.
  • Ingenol pictures
  • Ingenol
    30220-46-3
  • $400.00
  • 99%
  • Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd.

Ingenol Spectrum

Ingenol(30220-46-3)1HNMR

30220-46-3 (Ingenol) Related Search:

Cyclooctanone Cycloheptanone 1-NONEN-3-OL Cyclooctane ADOXAL
Cyclooctanemethanol 2-tert-Butylpropane-1,3-diol 3,5-Dimethyl-4-octanone 2,2,4-Trimethyl-3-pentanone Cycloheptene
3-Butene-1,2-diol (R)-(-)-1-Octen-3-ol, 99 Ingenol (Hydroxymethyl)cycloheptane 3,5-Dimethyl-4-heptanone
1-Hydroxymethyl-3-cyclopentene 2,2-Dimethyl-3-octanone Cyclopropylacetaldehyde

1of4

1A,2,5,5A,6,9,10,10A OCTAHYDRO-5,5A,6-TRIHYDROXY4(HYDROXYMETHYL)1,1,7,9-TETRAMETHYL1H-2,8 AMETHANOCYCLOPENTA[A]CYCLOPROPA[E]CYCLODECEN-11 ONE 1 ALPHA,2,5,5 ALPHA,6,9,10,10 ALPHA-OCTAHYDRO-5,5 ALPHA,6-TRIHYDROXY-4-HYDROXYMETHYL-1,1,7,9-RETRAMETHYL-1H-2,8 ALPHA-M INGENOL INGENOL \ ACTIVATES PROTEIN KINASE C (1ar,2s,5r,5ar,6s,8as,9r,10ar)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1h-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one INGENOL,HIGHPURITY 1alpha,2,5,5alpha,6,9,10,10alpha-Octahydro-5,5alpha,6-trihydroxy-4-hydroxymethyl-1,1,7,9,-retramethyl-1H-2,8alpha-m Ingenol 30220-46-3 HPLC 99% purity Ingenol from Euphorbia lathyris 30220-46-3 99% Purity Ingenol Natural Plant Extracts 30220-46-3 Euphorbia Source Ingenol, BR (1aR,2S,8aS)-1aα,2,5,5a,6,9,10,10aα-Octahydro-5β,5aβ,6β-trihydroxy-4-(hydroxymethyl)-1,1,7,9α-tetramethyl-2,8aα-methano-1H-cyclopenta[a]cyclopropa[e]cyclodecene-11-one (1aR,2S,8aS)-1aα,2,5,5a,6,9,10,10aα-Octahydro-5β,5aβ,6β-trihydroxy-4-hydroxymethyl-1,1,7,9α-tetramethyl-1H-2,8aα-methanocyclopenta[a]cyclopropa[e]cyclodecene-11-one Ingenol >99% Ingenol base (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-Trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one,1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxyMethyl)-1,1,7,9-tetraMethyl-,(1aR,2S,5R,5aR,6S,8aS,9R,10aR)- Ingenol USP/EP/BP Inglenook (-)-Ingenol Ingeno Giant Euphorbia Alcohol (1S,4S,5R,6R,9S,10R,12R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one Ingenol, 10 mM in DMSO 30220-46-3 BioChemical Cell Signaling and Neuroscience Cell Biology Protein Phosphorylation Protein Kinase Activators Activator