Rhododendrol Racemate
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MedKoo CAT#: 573633

CAS#: 69617-84-1 (racemate)

Description: Rhododendrol, (+/-)-, is an aromatic compound that may be useful in the treatment of hepatic diseases. However, this product is a known pro-oxidant which can be toxic to melanocytes.

Chemical Structure

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Rhododendrol Racemate
CAS# 69617-84-1 (racemate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 573633
Name: Rhododendrol Racemate
CAS#: 69617-84-1 (racemate)
Chemical Formula: C10H14O2
Exact Mass: 166.10
Molecular Weight: 166.220
Elemental Analysis: C, 72.26; H, 8.49; O, 19.25

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Related CAS #: 69617-84-1 (racemate)   501-96-2 (R-isomer)    

Synonym: AI3-31843; Rhododendrol, (+/-)-

IUPAC/Chemical Name: 4-(p-Hydroxyphenyl)butan-2-ol

InChi Key: SFUCGABQOMYVJW-UHFFFAOYSA-N

InChi Code: 1S/C10H14O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-8,11-12H,2-3H2,1H3

SMILES Code: CC(O)CCC1=CC=C(O)C=C1

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >3 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Rhododendrol competes with tyrosine for hydroxylation by tyrosinase and interferes with melanin synthesis. First, rhododendrol is catalysed by tyrosinase to produce toxic metabolites as rhododendrol-cyclic catechol. These reactive metabolites cause damage to the melanocytes.
In vitro activity: Rhododendrol-induced leukoderma is an autoimmune disorder, with rhododendrol as an environmental factor and HLA-DR4 as a genetic factor. Rhododendrol might be effective in treating melanomas. References: . Dermatology. 2016;232(1):44-9. https://pubmed.ncbi.nlm.nih.gov/26613259/
In vivo activity: Mice supplemented with rhododendrol have dramatically altered hepatic metabolisms concurrent with shifts in specific gut bacteria. Reference: Food Funct. 2022 Dec 13;13(24):13052-13063. https://pubmed.ncbi.nlm.nih.gov/36468583/

Preparing Stock Solutions

The following data is based on the product molecular weight 166.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Okura M, Yamashita T, Ishii-Osai Y, Yoshikawa M, Sumikawa Y, Wakamatsu K, Ito S. Effects of rhododendrol and its metabolic products on melanocytic cell growth. J Dermatol Sci. 2015 Nov;80(2):142-9. doi: 10.1016/j.jdermsci.2015.07.010. Epub 2015 Jul 26. PMID: 26282085. 2. Takagi R, Kawano M, Nakamura K, Tsuchida T, Matsushita S. T-Cell Responses to Tyrosinase-Derived Self-Peptides in Patients with Leukoderma Induced by Rhododendrol: Implications for Immunotherapy Targeting Melanoma. Dermatology. 2016;232(1):44-9. doi: 10.1159/000441217. Epub 2015 Nov 28. PMID: 26613259. 3. Li X, Wang Y, Yu C, Yao Y, Chen X, Deng ZY, Yao Z, Luo T. The signatures of liver metabolomics and gut microbiota in high-fat diet fed mice supplemented with rhododendrol. Food Funct. 2022 Dec 13;13(24):13052-13063. doi: 10.1039/d2fo01214f. PMID: 36468583. 4. Fushiya S, Kabe Y, Ikegaya Y, Takano F. (+)-rhododendrol and epi-rhododendrin suppress the NO production by activated macrophages in vivo. Planta Med. 1998 Oct;64(7):598-602. doi: 10.1055/s-2006-957529. PMID: 9810263.
In vitro protocol: 1. Okura M, Yamashita T, Ishii-Osai Y, Yoshikawa M, Sumikawa Y, Wakamatsu K, Ito S. Effects of rhododendrol and its metabolic products on melanocytic cell growth. J Dermatol Sci. 2015 Nov;80(2):142-9. doi: 10.1016/j.jdermsci.2015.07.010. Epub 2015 Jul 26. PMID: 26282085. 2. Takagi R, Kawano M, Nakamura K, Tsuchida T, Matsushita S. T-Cell Responses to Tyrosinase-Derived Self-Peptides in Patients with Leukoderma Induced by Rhododendrol: Implications for Immunotherapy Targeting Melanoma. Dermatology. 2016;232(1):44-9. doi: 10.1159/000441217. Epub 2015 Nov 28. PMID: 26613259.
In vivo protocol: 1. Li X, Wang Y, Yu C, Yao Y, Chen X, Deng ZY, Yao Z, Luo T. The signatures of liver metabolomics and gut microbiota in high-fat diet fed mice supplemented with rhododendrol. Food Funct. 2022 Dec 13;13(24):13052-13063. doi: 10.1039/d2fo01214f. PMID: 36468583. 2. Fushiya S, Kabe Y, Ikegaya Y, Takano F. (+)-rhododendrol and epi-rhododendrin suppress the NO production by activated macrophages in vivo. Planta Med. 1998 Oct;64(7):598-602. doi: 10.1055/s-2006-957529. PMID: 9810263.

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1: Ito S, Wakamatsu K. Biochemical Mechanism of Rhododendrol-Induced Leukoderma. Int J Mol Sci. 2018 Feb 12;19(2). pii: E552. doi: 10.3390/ijms19020552. Review. PubMed PMID: 29439519; PubMed Central PMCID: PMC5855774.

2: Ito S, Okura M, Wakamatsu K, Yamashita T. The potent pro-oxidant activity of rhododendrol-eumelanin induces cysteine depletion in B16 melanoma cells. Pigment Cell Melanoma Res. 2017 Jan;30(1):63-67. doi: 10.1111/pcmr.12556. PubMed PMID: 28132436.

3: Kondo M, Kawabata K, Sato K, Yamaguchi S, Hachiya A, Takahashi Y, Inoue S. Glutathione maintenance is crucial for survival of melanocytes after exposure to rhododendrol. Pigment Cell Melanoma Res. 2016 Sep;29(5):541-9. doi: 10.1111/pcmr.12494. Epub 2016 Jul 1. PubMed PMID: 27223685.